barclaysd18rn0p25nwr6d.cloudfront.net/cik-0001224608/9e5db933-0... · 2019-05-28 · income and...

111
Use these links to rapidly review the document TABLE OF CONTENTS TABLE OF CONTENTS Table of Contents Filed Pursuant to Rule 424(b)(5) Registration Statement No. 333-224830 The information in this prospectus supplement is not complete and may be changed. This preliminary prospectus supplement and the accompanying prospectus are not an offer to sell these securities and are not soliciting an offer to buy these securities in any jurisdiction where the offer or sale is not permitted. SUBJECT TO COMPLETION, DATED MAY 28, 2019 Prospectus Supplement to Prospectus dated May 10, 2018. $425,000,000 CNO Financial Group, Inc. % Senior Notes due 2029 CNO Financial Group, Inc., a Delaware corporation ("CNO"), is offering $425,000,000 aggregate principal amount of % senior notes due 2029 (the "Notes"). The Notes will mature on , 2029. CNO will pay interest on the Notes on and of each year, commencing on , 2020. The Notes will be issued only in minimum denominations of $2,000 and integral multiples of $1,000 in excess thereof. Prior to , 2029, CNO may redeem some or all of the Notes at any time or from time to time at a "make-whole" redemption price plus accrued and unpaid interest. On or after , 2029, CNO may redeem some or all of the Notes at any time or from time to time at a redemption price equal to 100% of the principal amount of any Notes to be redeemed plus accrued and unpaid interest. See "Description of the Notes—Optional Redemption." The Notes will be CNO's senior unsecured obligations and will rank equally with CNO's other senior unsecured and unsubordinated debt from time to time outstanding. The Notes will be effectively subordinated to all of CNO's future indebtedness that is secured, to the extent of the value of the assets securing such indebtedness. The Notes will be structurally subordinated to all existing and future indebtedness and other liabilities of CNO's subsidiaries. See "Risk Factors" beginning on page S-17 to read about important factors you should consider before buying the Notes. Neither the Securities and Exchange Commission nor any other regulatory body has approved or disapproved of these securities or passed upon the accuracy or adequacy of this prospectus supplement or the accompanying prospectus. Any representation to the contrary is a criminal offense. Per Note Total Public offering price % $ Underwriting discount* % $ Proceeds, before expenses, to CNO % $ * We refer you to the "Underwriting" section beginning on page S-52 of this prospectus supplement for additional information regarding underwriting compensation. The initial public offering price set forth above does not include accrued interest, if any. Interest on the Notes will accrue from , 2019 and must be paid by the purchasers if such Notes are delivered after , 2019. The underwriters expect to deliver the Notes through the facilities of The Depository Trust Company against payment in New York, New York on , 2019. Joint Book-Running Managers

Upload: others

Post on 31-Mar-2020

0 views

Category:

Documents


0 download

TRANSCRIPT

Page 1: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

UsetheselinkstorapidlyreviewthedocumentTABLEOFCONTENTSTABLEOFCONTENTS

TableofContents

Filed Pursuant to Rule 424(b)(5) Registration Statement No. 333-224830

The information in this prospectus supplement is not complete and may be changed. This preliminary prospectus supplement and the accompanyingprospectus are not an offer to sell these securities and are not soliciting an offer to buy these securities in any jurisdiction where the offer or sale is notpermitted.

SUBJECT TO COMPLETION, DATED MAY 28, 2019

Prospectus Supplement to Prospectus dated May 10, 2018.

$425,000,000

CNO Financial Group, Inc. % Senior Notes due 2029

CNOFinancialGroup,Inc.,aDelawarecorporation("CNO"),isoffering$425,000,000aggregateprincipalamountof%seniornotesdue2029(the"Notes").TheNoteswillmatureon,2029.CNOwillpayinterestontheNotesonandofeachyear,commencingon,2020.TheNoteswillbeissuedonlyinminimumdenominationsof$2,000andintegralmultiplesof$1,000inexcessthereof.Priorto,2029,CNOmayredeemsomeoralloftheNotesatanytimeorfromtimetotimeata"make-whole"redemptionpriceplusaccruedandunpaidinterest.Onorafter,2029,CNOmayredeemsomeoralloftheNotesatanytimeorfromtimetotimeataredemptionpriceequalto100%oftheprincipalamountofanyNotestoberedeemedplusaccruedandunpaidinterest.See"DescriptionoftheNotes—OptionalRedemption."

TheNoteswillbeCNO'sseniorunsecuredobligationsandwillrankequallywithCNO'sotherseniorunsecuredandunsubordinateddebtfromtimetotimeoutstanding.TheNoteswillbeeffectivelysubordinatedtoallofCNO'sfutureindebtednessthatissecured,totheextentofthevalueoftheassetssecuringsuchindebtedness.TheNoteswillbestructurallysubordinatedtoallexistingandfutureindebtednessandotherliabilitiesofCNO'ssubsidiaries.

See "Risk Factors" beginning on page S-17 to read about important factors you should consider before buying theNotes.

Neither the Securities and Exchange Commission nor any other regulatory body has approved or disapproved of these securities or passed upon theaccuracy or adequacy of this prospectus supplement or the accompanying prospectus. Any representation to the contrary is a criminal offense.

Per Note Total

Publicofferingprice % $

Underwritingdiscount* % $

Proceeds,beforeexpenses,toCNO % $

* Wereferyoutothe"Underwriting"sectionbeginningonpageS-52ofthisprospectussupplementforadditionalinformationregardingunderwritingcompensation.

Theinitialpublicofferingpricesetforthabovedoesnotincludeaccruedinterest,ifany.InterestontheNoteswillaccruefrom,2019andmustbepaidbythepurchasersifsuchNotesaredeliveredafter,2019.

TheunderwritersexpecttodelivertheNotesthroughthefacilitiesofTheDepositoryTrustCompanyagainstpaymentinNewYork,NewYorkon,2019.

JointBook-RunningManagers

Page 2: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

Co-Managers

ProspectusSupplementdated,2019.

Goldman Sachs & Co. LLC Barclays KeyBanc Capital Markets RBC Capital Markets

BofA Merrill Lynch Deutsche Bank Securities

Page 3: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

TABLE OF CONTENTS

Prospectus Supplement

Prospectus

S-i

Page AboutThisProspectusSupplement S-iiPresentationofFinancialData;Non-GaapFinancialMeasures S-iiIndustryandMarketData S-iiiWhereYouCanFindMoreInformation S-iiiIncorporationofCertainInformationbyReference S-ivForward-LookingStatements S-vSummary S-1RiskFactors S-17UseofProceeds S-24Capitalization S-25DescriptionofOtherIndebtedness S-26DescriptionofNotes S-29CertainUnitedStatesFederalIncomeandEstateTaxConsequencestoNon-U.S.Holders S-51CertainERISAConsiderations S-55Underwriting S-57ValidityofSecurities S-62Experts S-62

Page ABOUTTHISPROSPECTUS 1WHEREYOUCANFINDMOREINFORMATION 3INCORPORATIONOFCERTAININFORMATIONBYREFERENCE 4FORWARD-LOOKINGSTATEMENTS 5OURCOMPANY 8RISKFACTORS 9RATIOSOFEARNINGSTOFIXEDCHARGES 10USEOFPROCEEDS 11DESCRIPTIONOFDEBTSECURITIES 12DESCRIPTIONOFCAPITALSTOCK 22DESCRIPTIONOFDEPOSITARYSHARES 29DESCRIPTIONOFWARRANTS 32DESCRIPTIONOFPURCHASECONTRACTS 34DESCRIPTIONOFUNITS 34PLANOFDISTRIBUTION 35VALIDITYOFTHESECURITIES 37EXPERTS 37

Page 4: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

You should rely only on the information contained or incorporated by reference in this prospectus supplement, the accompanying prospectus or inany free writing prospectus filed by us with the Securities and Exchange Commission (the "SEC"). Neither we nor the underwriters have authorizedanyone else to provide you with different or additional information or make any representation other than what is contained or incorporated by referencein this prospectus supplement, the accompanying prospectus or in any free writing prospectuses we have prepared. If anyone provides you with differentor inconsistent information, you should not rely on it. Neither we nor the underwriters are making an offer to sell these securities in any jurisdictionwhere the offer and sale is not permitted. You should assume that the information in this prospectus supplement, the accompanying prospectus, any suchfree writing prospectus or any document incorporated by reference is accurate only as of the date of the applicable document. Our business, financialcondition, results of operations and prospects may have changed since that date.

It is expected that delivery of the Notes will be made against payment therefor on or about , 2019, which will be the business dayfollowing the date of pricing of the Notes (such settlement period being herein referred to as T+ ). Purchasers of Notes should be aware that the abilityto settle secondary market trades of the Notes effected on the date of pricing may be affected by the T+ settlement.

ABOUT THIS PROSPECTUS SUPPLEMENT

Asusedinthisprospectussupplement,unlessotherwisespecifiedorunlessthecontextindicatesotherwise,referencesinthisprospectussupplementto:

• "CNO"orthe"holdingcompany"referonlytoCNOFinancialGroup,Inc.onanunconsolidatedbasis.PriortoitsnamechangeinMay2010,CNOwasformerlyknownasConseco,Inc.,aDelawarecorporation.CNObecamethesuccessortoConseco,Inc.,anIndianacorporation(our"Predecessor"),inconnectionwithourbankruptcyreorganizationwhichbecameeffectiveonSeptember10,2003;and

• "CNOFinancialGroup,"the"Company,""we,""us,"and"our"refertoCNOanditssubsidiariesonaconsolidatedbasisor,whenthecontextrequiresotherwise,ourPredecessoranditssubsidiariesonaconsolidatedbasis.

Thisdocumentisintwoparts.Thefirstpartisthisprospectussupplementwhichcontainsspecificinformationaboutthetermsofthisoffering.Thisprospectussupplementalsoaddsandupdatesinformationcontainedintheaccompanyingprospectus.Thesecondpart,theaccompanyingprospectus,providesmoregeneralinformationaboutusandsecuritieswemayofferfromtimetotime,someofwhichmaynotapplytothisofferingofsecurities.Ifthereisanyinconsistencybetweentheinformationinthisprospectussupplementandtheaccompanyingprospectus,youshouldrelyontheinformationinthisprospectussupplement.

PRESENTATION OF FINANCIAL DATA; NON-GAAP FINANCIAL MEASURES

Unlessotherwisespecified,thefinancialdatafortheCompany(otherthanstatutorydata)includedorincorporatedbyreferenceinthisprospectussupplementhasbeenpreparedinaccordancewithaccountingprinciplesgenerallyacceptedintheUnitedStates("GAAP").Thestatutorydataincludedorincorporatedbyreferenceinthisprospectussupplementhasbeenderivedfromthestatementsfiledbyourinsurancesubsidiarieswithregulatoryauthoritiesandpreparedinaccordancewithstatutoryaccountingpractices,whichvaryincertainrespectsfromGAAP.Inaddition,wheresoindicatedinthisprospectussupplement,wehaveusedcertainfinancialmeasuresthatarenotcalculatedinaccordancewithGAAPtoassessthefinancialperformanceoftheCompany,includingAdjustedEBIT,netoperatingincomeanddebttototalcapitalratio(excludingaccumulatedothercomprehensiveincome).Weusesuchnon-GAAPfinancialmeasuresbecausewebelievethattheyaremeaningfulmeasuresof

S-ii

Page 5: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

theCompany'sperformance.Ourmethodofcalculatingthesenon-GAAPfinancialmeasuresmaydifferfromthemethodsusedbyothercompaniesand,asaresult,thenon-GAAPfinancialmeasurespresentedinthisprospectussupplementmaynotbecomparabletoothersimilarlytitledmeasuresdisclosedbyothercompanies.See"Summary—SummaryHistoricalandUnauditedProFormaConsolidatedFinancialandOperatingData."

Priortothethirdquarterof2018,wemanagedourbusinessthroughthefollowingoperatingsegments:BankersLife,WashingtonNationalandColonialPenn,whicharedefinedonthebasisofproductdistribution;long-termcareinrun-off(consistingofthelong-termcarebusinessthatwasrecapturedduetotheterminationofcertainreinsuranceagreementseffectiveSeptember30,2016);andcorporateoperations,comprisedofholdingcompanyactivitiesandcertainnoninsurancecompanybusinesses.

OnSeptember27,2018,wecompletedalong-termcarereinsurancetransaction(the"ReinsuranceTransaction")pursuanttowhichourwholly-ownedsubsidiary,BankersLifeandCasualtyCompany,enteredintoanagreementwithWiltonReassuranceCompany("WiltonRe")tocedeallofitslegacy(priorto2003)comprehensiveandnursinghomelong-termcarepolicies(withstatutoryreservesof$2.7billion)through100%indemnitycoinsurance,asfurtherdescribedinthenoteentitled"Reinsurance"totheconsolidatedfinancialstatementsincorporatedbyreferencefromourAnnualReportonForm10-KfortheyearendedDecember31,2018.Inanticipationofthereinsuranceagreement,wereorganizedourbusinesssegmentstomovetheblocktobecededfromthe"BankersLifesegment"tothe"Long-termcareinrun-offsegment"inthethirdquarterof2018.Allpriorperiodsegmentdisclosuresincludedinthisprospectussupplementhavebeenrevisedtoconformtomanagement'scurrentviewoftheCompany'soperatingsegments.

Formoreinformation,seethesectionentitled"Summary—SummaryHistoricalandUnauditedProFormaConsolidatedFinancialandOperatingData"includedinthisprospectussupplementaswellastheinformationsetforthunder"Management'sDiscussionandAnalysisofConsolidatedFinancialConditionandResultsofOperations"incorporatedbyreferencefromourQuarterlyReportonForm10-QforthequarterendedMarch31,2019andourAnnualReportonForm10-KfortheyearendedDecember31,2018andtheCompany'sconsolidatedfinancialstatementsandrelatednotestheretoincorporatedbyreferenceintothisprospectussupplement.

INDUSTRY AND MARKET DATA

Wehaveobtainedsomeindustryandmarketsharedatafromthird-partysourcesthatwebelievearereliable.Inmanycases,however,wehavemadestatementsinthisprospectussupplementandthedocumentsincorporatedbyreferenceregardingourindustryandourpositionintheindustrybasedonestimatesmadefromourexperienceintheindustryandourowninvestigationofmarketconditions.Webelievetheseestimatestobeaccurateasofthedateofthisprospectussupplement.However,thisinformationmayprovetobeinaccuratebecauseofthemethodbywhichweobtainedsomeofthedataforourestimatesorbecausethisinformationcannotalwaysbeverifiedwithcompletecertaintyduetothelimitsontheavailabilityandreliabilityofrawdata,thevoluntarynatureofthedatagatheringprocessandotherlimitationsanduncertainties.Asaresult,youshouldbeawarethattheindustryandmarketdataincludedin,orincorporatedbyreferenceinto,thisprospectussupplement,andestimatesandbeliefsbasedonthatdata,maynotbereliable.Wecannot,andtheunderwriterscannot,guaranteetheaccuracyorcompletenessofanysuchinformation.

WHERE YOU CAN FIND MORE INFORMATION

CNOfilesreports,proxystatementsandotherinformationwiththeSEC.Thesereports,proxystatementsandotherinformationcanbereadandcopiedattheSEC'spublicreferenceroomat100FStreet,N.E.,Washington,D.C.20549.PleasecalltheSECat1-800-SEC-0330forfurther

S-iii

Page 6: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

informationontheoperationofthepublicreferenceroom.TheSECmaintainsaninternetsiteatwww.sec.govthatcontainsreports,proxyandinformationstatementsandotherinformationregardingcompaniesthatfileelectronicallywiththeSEC,includingCNO.CNO'scommonstockislistedandtradingontheNewYorkStockExchange(the"NYSE")underthesymbol"CNO."Thesereports,proxystatementsandotherinformationcanalsobereadattheofficesoftheNYSE,11WallStreet,NewYork,NewYork10005.

WehavefiledwiththeSECaregistrationstatementundertheSecuritiesActof1933,asamended(the"SecuritiesAct")onFormS-3withrespecttotheNotesandcertainothersecurities.Thisprospectussupplementandtheaccompanyingprospectusdonotcontainalltheinformationsetforthintheregistrationstatementanditsexhibits,partsofwhichareomittedinaccordancewiththerulesandregulationsoftheSEC.ForfurtherinformationwithrespecttousandtheNotes,referenceismadetotheregistrationstatementandtotheexhibits.Statementsinthisprospectussupplementaboutthecontentsofanycontract,agreementorotherdocumentarenecessarilynotcompleteand,ineachinstance,wereferyoutothecopyofsuchcontract,agreementordocumentfiledasanexhibittotheregistrationstatement,witheachsuchstatementbeingqualifiedinallrespectbyreferencetothedocumenttowhichitrefers.

INCORPORATION OF CERTAIN INFORMATION BY REFERENCE

Inthisprospectussupplement,CNO"incorporatesbyreference"theinformationthatitfileswiththeSEC,whichmeansthatCNOcandiscloseimportantinformationtoyoubyreferringyoutoadocumentthatitfiledwiththeSEC.Theinformationsoincorporatedbyreferenceisconsideredtobeapartofthisprospectussupplement,andinformationthatCNOfileslaterwiththeSECwillautomaticallyupdateandsupersedethisinformation.Anyinformationcontainedinthisprospectussupplementupdatesand,whereapplicable,supersedestheinformationinthedocumentsincorporatedbyreferencehereinlistedbelow.CNOincorporatesbyreferencethedocumentslistedbelowandanyfilingsmadewiththeSECunderSections13(a),13(c),14or15(d)oftheSecuritiesExchangeActof1934,asamended(the"ExchangeAct")(excludinganyCurrentReportsonForm8-KcontaininganydisclosurepursuanttoItem2.02orItem7.01unlessotherwiseindicated),afterthedateofthisprospectussupplementanduntilthesettlementoftheofferingoftheNotes:

• AnnualReportonForm10-KfortheyearendedDecember31,2018;

• QuarterlyReportonForm10-QforthequarterendedMarch31,2019;

• PortionsofourDefinitiveProxyStatementonSchedule14AfiledonMarch27,2019thatareincorporatedbyreferenceintoPartIIIofourForm10-KforthefiscalyearendedDecember31,2018,filedonFebruary26,2019;and

• CurrentReportsonForm8-KfiledonMarch18,2019,April29,2019(solelywithrespecttoItem8.01therein),May10,2019andMay28,2019.

Anystatementcontainedinadocumentincorporatedordeemedtobeincorporatedbyreferenceinthisprospectussupplementandtheaccompanyingprospectuswillbedeemedtobemodifiedorsupersededtotheextentthatastatementcontainedhereinorinanyothersubsequentlyfileddocumentwhichalsoisorisdeemedtobeincorporatedbyreferenceinthisprospectussupplementmodifiesorsupersedesthatstatement.Anystatementsomodifiedorsupersededwillnotbedeemed,exceptassomodifiedorsuperseded,toconstituteapartofthisprospectussupplementandtheaccompanyingprospectus.

CNOwillprovidewithoutchargeuponwrittenororalrequest,acopyofanyorallofthedocumentsthatareincorporatedbyreferenceintothisprospectussupplement,otherthanexhibitstothosedocuments,unlessthoseexhibitsarespecificallyincorporatedbyreferenceintothosedocuments.RequestsshouldbedirectedtoCNOatInvestorRelations,CNOFinancialGroup,Inc.,11825N.PennsylvaniaStreet,Carmel,Indiana46032,(317)817-2893.YoumayalsoobtainthedocumentsincorporatedbyreferenceintothisprospectussupplementasofthedatehereofatCNO'swebsite,www.cnoinc.com.AllotherinformationcontainedonoraccessiblethroughCNO'swebsiteisnotapartofthisdocument.

S-iv

Page 7: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

FORWARD-LOOKING STATEMENTS

Ourstatements,trendanalysesandotherinformationcontainedinthisprospectussupplementandthedocumentsincorporatedbyreferencecontainforward-lookingstatementswithinthemeaningofthefederalsecuritieslawsandthePrivateSecuritiesLitigationReformActof1995.Forward-lookingstatementstypicallyareidentifiedbytheuseoftermssuchas"anticipate,""believe,""plan,""estimate,""expect,""project,""intend,""may,""will,""would,""contemplate,""possible,""attempt,""seek,""should,""could,""goal,""target,""ontrack,""comfortablewith,""optimistic,""guidance,""outlook"andsimilarwords,althoughsomeforward-lookingstatementsareexpresseddifferently.Youshouldconsiderstatementsthatcontainthesewordscarefullybecausetheydescribeourexpectations,plans,strategiesandgoalsandourbeliefsconcerningfuturebusinessconditions,ourresultsofoperations,financialposition,andourbusinessoutlookortheystateother"forward-looking"informationbasedoncurrentlyavailableinformation.The"RiskFactors"sectionofourAnnualReportonForm10-KfortheyearendedDecember31,2018,whichisincorporatedbyreferenceintothisprospectussupplement,providesexamplesofrisks,uncertaintiesandeventsthatcouldcauseouractualresultstodiffermateriallyfromtheexpectationsexpressedinourforward-lookingstatements.Assumptionsandotherimportantfactorsthatcouldcauseouractualresultstodiffermateriallyfromthoseanticipatedinourforward-lookingstatementsinclude,amongotherthings:

• changesinorsustainedlowinterestratescausingreductionsininvestmentincome,themarginsofourfixedannuityandlifeinsurancebusinesses,andsalesof,anddemandfor,ourproducts;

• expectationsoflowerfutureinvestmentearningsmaycauseustoaccelerateamortization,writedownthebalanceofinsuranceacquisitioncostsorestablishadditionalliabilitiesforinsuranceproducts;

• generaleconomic,marketandpoliticalconditionsanduncertainties,includingtheperformanceandfluctuationsofthefinancialmarketswhichmayaffectthevalueofourinvestmentsaswellasourabilitytoraisecapitalorrefinanceexistingindebtednessandthecostofdoingso;

• theultimateoutcomeoflawsuitsfiledagainstusandotherlegalandregulatoryproceedingstowhichwearesubject;

• ourabilitytomakeanticipatedchangestocertainnon-guaranteedelementsofourlifeinsuranceproducts;

• ourabilitytoobtainadequateandtimelyrateincreasesonourhealthproducts,includingourlong-termcarebusiness;

• thereceiptofanyrequiredregulatoryapprovalsfordividendandsurplusdebentureinterestpaymentsfromourinsurancesubsidiaries;

• mortality,morbidity,theincreasedcostandusageofhealthcareservices,persistency,theadequacyofourpreviousreserveestimates,changesinthehealthcaremarketandotherfactorswhichmayaffecttheprofitabilityofourinsuranceproducts;

• changesinourassumptionsrelatedtodeferredacquisitioncostsorthepresentvalueoffutureprofits;

• therecoverabilityofourdeferredtaxassetsandtheeffectofpotentialownershipchangesandtaxratechangesontheirvalue;

• ourassumptionthatthepositionswetakeonourtaxreturnfilingswillnotbesuccessfullychallengedbytheInternalRevenueService;

• changesinaccountingprinciplesandtheinterpretationthereof;

S-v

Page 8: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

• ourabilitytocontinuetosatisfythefinancialratioandbalancerequirementsandothercovenantsofourdebtagreements;

• ourabilitytoachieveanticipatedexpensereductionsandlevelsofoperationalefficienciesincludingimprovementsinclaimsadjudicationandcontinuedautomationandrationalizationofoperatingsystems;

• performanceandvaluationofourinvestments,includingtheimpactofrealizedlosses(includingother-than-temporaryimpairmentcharges);

• ourabilitytoidentifyproductsandmarketsinwhichwecancompeteeffectivelyagainstcompetitorswithgreatermarketshare,higherratings,greaterfinancialresourcesandstrongerbrandrecognition;

• ourabilitytogeneratesufficientliquiditytomeetourdebtserviceobligationsandothercashneeds;

• changesincapitaldeploymentopportunities;

• ourabilitytomaintaineffectivecontrolsoverfinancialreporting;

• ourabilitytocontinuetorecruitandretainproductiveagentsanddistributionpartners;

• customerresponsetonewproducts,distributionchannelsandmarketinginitiatives;

• ourabilitytoachieveadditionalupgradesofourfinancialstrengthratingsandourinsurancecompanysubsidiariesaswellastheimpactofourratingsonourbusiness,ourabilitytoaccesscapital,andthecostofcapital;

• regulatorychangesoractions,includingthoserelatingtoregulationofthefinancialaffairsofourinsurancecompanies,suchasthecalculationofrisk-basedcapitalandminimumcapitalrequirements,andpaymentofdividendsandsurplusdebentureinteresttous;regulationofthesale,underwritingandpricingofproducts;andhealthcareregulationaffectinghealthinsuranceproducts;

• changesinthefederalincometaxlawsandregulationswhichmayaffectoreliminatetherelativetaxadvantagesofsomeofourproductsoraffectthevalueofourdeferredtaxassets;

• availabilityandeffectivenessofreinsurancearrangements,aswellastheimpactofanydefaultsorfailureofreinsurerstoperform;

• theperformanceofthirdpartyserviceprovidersandpotentialdifficultiesarisingfromoutsourcingarrangements;

• thegrowthrateofsales,collectedpremiums,annuitydepositsandassets;

• interruptionintelecommunication,informationtechnologyorotheroperationalsystemsorfailuretomaintainthesecurity,confidentialityorprivacyofsensitivedataonsuchsystems;

• eventsofterrorism,cyberattacks,naturaldisastersorothercatastrophicevents,includinglossesfromadiseasepandemic;

• ineffectivenessofriskmanagementpoliciesandproceduresinidentifying,monitoringandmanagingrisks;

• completionofthisoffering;and

• theriskfactorsoruncertaintieslistedfromtimetotimeinourfilingswiththeSEC.

S-vi

Page 9: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Otherfactorsandassumptionsnotidentifiedabovearealsorelevanttotheforward-lookingstatements,andiftheyproveincorrect,couldalsocauseactualresultstodiffermateriallyfromthoseprojected.

Allwrittenororalforward-lookingstatementsattributabletousareexpresslyqualifiedintheirentiretybytheforegoingcautionarystatement.Ourforward-lookingstatementsspeakonlyasofthedatemade.Weassumenoobligationtoupdateortopubliclyannouncetheresultsofanyrevisionstoanyoftheforward-lookingstatementstoreflectactualresults,futureeventsordevelopments,changesinassumptionsorchangesinotherfactorsaffectingtheforward-lookingstatements.

Thereportingofrisk-basedcapital("RBC")measuresisnotintendedforthepurposeofrankinganyinsurancecompanyorforuseinconnectionwithanymarketing,advertisingorpromotionalactivities.

S-vii

Page 10: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

SUMMARY

ThissummaryhighlightsinformationcontainedelsewhereinthisprospectussupplementandthereforeisnotcompleteanddoesnotcontainalltheinformationthatyoushouldconsiderbeforeinvestingintheNotes.Youshouldreadthisentiredocumentcarefully,includingtheinformationundertheheading"RiskFactors"andtheotherinformationincludedin,orincorporatedbyreferenceinto,thisprospectussupplement,includingourfinancialstatementsandrelatednotes,beforemakinganinvestmentdecision.See"IncorporationofCertainInformationbyReference."

CNO Financial Group

CNOisaholdingcompanyforagroupofinsurancecompaniesoperatingthroughouttheUnitedStatesthatdevelop,marketandadministerhealthinsurance,annuity,individuallifeinsuranceandotherinsuranceproducts.

Wefocusonservingmiddle-incomepre-retireeandretiredAmericans,whichwebelieveareattractive,underserved,highgrowthmarkets.Wesellourproductsthroughthreedistributionchannels:careeragents,independentproducers(someofwhomselloneormoreofourproductlinesexclusively)anddirectmarketing.Oursubsidiariesgeneratestrongfreecashflowandwebenefitfromrecurringrevenues.AsofMarch31,2019,wehadapproximately3.2millioninsurancepoliciesinforceanda$23.7billioninvestmentportfolio,whichproviderecurringpremiumsandinvestmentincome,respectively.CNOisapubliclylistedcompany(NYSE:CNO)andhadamarketcapitalizationof$2.6billionasofMarch31,2019.

OnSeptember27,2018,wecompletedalong-termcarereinsurancetransaction(the"ReinsuranceTransaction")pursuanttowhichourwholly-ownedsubsidiary,BankersLifeandCasualtyCompany("BankersLife"),enteredintoanagreementwithWiltonRetocedeallofitslegacy(priorto2003)comprehensiveandnursinghomelong-termcarepolicies(withstatutoryreservesof$2.7billion)through100%indemnitycoinsurance.Thetransactionrepresented52%ofCNO'sstatutorylong-termcarereserves.TheReinsuranceTransactionwasatransformativestepforCNOandtheculminationofamulti-yearexplorationofstrategicalternatives.Itreducesriskandthepotentialfutureearningsvolatilityresultingfromthelegacyblockofbusiness.InanticipationofthecompletionoftheReinsuranceTransaction,wereorganizedourbusinesssegmentstomovetheblocktobecededfromthe"BankersLifesegment"tothe"Long-termcareinrun-offsegment"inthethirdquarterof2018.Allpriorperiodsegmentdisclosuresinthisprospectussupplementhavebeenrevisedtoconformtomanagement'scurrentviewoftheCompany'soperatingsegments.

ForthetwelvemonthsendedMarch31,2019,wehad$4.3billionofrevenuesandanetlossof$347.5million(includingalossof$661.1millionrelatedtotheReinsuranceTransaction).ForthetwelvemonthsendedMarch31,2019,onaproformabasistogiveeffecttoeventsthataredirectlyattributabletotheReinsuranceTransactionasiftheReinsuranceTransactionoccurredbeforeJanuary1,2018wegenerated$3.8billionofrevenuesand$304.0millionofnetincome.See"—SummaryHistoricalandUnauditedProFormaConsolidatedFinancialandOperatingData"forthecalculationofdataforthetwelvemonthsendedMarch31,2019.AtMarch31,2019,ourdebttototalcapitalratio(excludingaccumulatedothercomprehensiveincome)wouldhavebeen22.3%onanasadjustedbasistogiveeffecttothisoffering.

S-1

Page 11: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

OurSegmentsandProducts

ForthetwelvemonthsendedMarch31,2019,wehad$3.8billionofcollectedpremiums.ThefollowingchartssetforththepercentagesofpremiumscollectedduringthetwelvemonthsendedMarch31,2019bysegmentandproduct:

Note:$85.0millionofthecollectedpremiumsintheLong-termcareinrun-offsegmentrelatedtobusinessthatwascededtoWiltonRe.

Ourinsurancesegmentsaredescribedbelow:

• BankersLife:Underwrites,marketsanddistributesMedicaresupplementinsurance,interest-sensitivelifeinsurance,traditionallifeinsurance,fixedannuitiesandlong-termcareinsuranceproductstothemiddle-incomeseniormarketthroughadedicatedfieldforceofcareeragents,financialandinvestmentadvisors,andsalesmanagerssupportedbyanetworkofcommunity-basedsalesoffices.AtMarch31,2019,BankersLifehadover4,200producingagentswithover260locationsnationwide.

• WashingtonNational:Underwrites,marketsanddistributessupplementalhealthinsurance(includingspecifieddisease,accidentandhospitalindemnityinsuranceproducts)andlifeinsurancetomiddle-incomeconsumersathomeandattheworksiteprimarilythroughourwholly-ownedmarketingorganization(whichhadapproximately700producingagentsatMarch31,2019).

• ColonialPenn:Marketsprimarilygradedbenefitandsimplifiedissuelifeinsurancedirectlytocustomersintheseniormiddle-incomemarketthroughtelevisionadvertising,directmail,theinternetandtelemarketing.

• Long-termcareinrun-off:Consistsofblocksoflong-termcarebusinesswhicharenotactivelymarketedandhavebeenplacedinrun-off.Specificcomponentsinclude:(i)thelong-termcarebusinessthatwasrecapturedduetotheterminationofcertainreinsuranceagreementseffectiveSeptember30,2016(suchbusinesswasissuedoracquiredbyWashingtonNationalandBankersConsecoLifeInsuranceCompany);and(ii)certainlegacy(priorto2003)comprehensiveandnursinghomelong-termcarepolicies(suchbusinesswasissuedbyBankersLife)whichwascededinSeptember2018pursuanttotheReinsuranceTransaction.

S-2

Page 12: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Ourproductsaredescribedbelow:

Ourhealthinsuranceproductsareprimarilycomprisedof:

• Medicaresupplementpolicies:coverageforvarioushospitalandmedicalexpensesthatarenotcoveredunderthefederalMedicareprogramandspecifiedlosseswhichexceedthefederalprogram'smaximumbenefits.WeprimarilymarketthepolicieswithafocusonindividualswhohaverecentlybecomeeligibleforMedicarebyreachingtheageof65.

• Long-termcarepolicies:coveragefornursinghomes,homehealthcare,oracombinationofboth.Inthethirdquarterof2018,weceasedsalesofhomehealthcareonlylong-termcarepolicies.Inaddition,weceasedsalesofcomprehensiveandnursinghomelong-termcarepolicieswithbenefitperiodsexceedingthreeyears.

• Supplementalhealthproducts:policiesprovidingfixedorlimitedhealthbenefitsforcriticalillnesses.

Ourannuityproductsareprimarilycomprisedof:

• Fixedindexannuities

• Otherfixedinterestannuities:fixedratesingle-premiumdeferredannuities,flexiblepremiumdeferredannuitiesandsingle-premiumimmediateannuities.

Ourlifeinsuranceproductsareprimarilycomprisedof:

• Interest-sensitivelifeproducts:universallifeandotherinterest-sensitivelifeproductsthatprovidelifeinsurancewithadjustableratesofreturnrelatedtocurrentinterestrates.

• Traditionallifeproducts:wholelife,gradedbenefitlife,termlifeandsinglepremiumwholelifeproducts.

Our Strengths

WellPositionedinMiddle-IncomeMarket,withSustainableGrowthInitiatives

Weareoneoftheleadingnationalprovidersoflifeandhealthinsuranceproductsfocusedprimarilyonmiddle-incomepre-retireeandretiredAmericans,whichwebelieveareattractive,underserved,highgrowthmarketsrelativetoothersegmentsoftheinsurancemarket.

Oursegmentedmarketstrategyandrecognizablebrandsaredesignedtocapitalizeontheseunderservedmarkets.Webelievethefollowingcapabilitiesareintegraltoexistingandcontinuedsuccessinthemarketsweserve:

• extensiveexperienceandunderstandingofthemiddle-incomemarketfromourhistoryofbeingaleadingproviderofprotectionandaccumulationproducts.

• differentiatedofferingviaatargetedmarketversusproductfocus.

• diversificationofproductsanddistributionchannels.

• positionedtohelpcustomerstoaddressmainconcernsofoutlivingtheirassetsanddealingwithrisinghealthcarecostsastheyage.

Tosupplementourstrongmiddle-incomemarketfocus,wehavedevelopedongoinginitiativestodriveprofitableexpansion,includingthelaunchofnewproducts.Theinitiativesarecenteredaroundourgrowthstrategytobroadenourdemographicreach,enhanceandexpandourproductportfolioandtocapitalizeonopportunitiestoinvestinourbusinessoracquisitiontransactions.

S-3

Page 13: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Inadditiontoourgrowthinitiatives,wehaveanumberofstrategieswithineachofoursegmentstofurtherdriveorganicgrowthinthebusiness:

• BankersLife:continueexpandingandenhancingourbroker-dealerandregisteredinvestmentadvisorprogram,developouragencyforcewithenhancedagentsupportandtraining,andfocusonretainingexperiencedagents.

• WashingtonNational:broadenourgeographicreach,advanceworksitecapabilities,expandindependentdistributionandimprovebrandawareness.

• ColonialPenn:simplifyissueunderwritingenhancements,expandwebanddigitalpresenceandleveragelead-sharingcross-salesopportunities.

DiversifiedLiabilityPortfoliowithActiveRiskManagement

Weemployacomprehensiveriskmanagementstrategywhichisembeddedinouroperationsanddecisionmakingprocesses.Ourviewonriskandrisktolerancesarecontinuallyevaluatedandarecentraltoouroperations.Wefurthersupplementthiswithdisciplinedpricingandreviewofactuarialassumptions,company-widestresstestsandongoingmonitoringofemergingactuarialexperience,assetexposureandoperationalrisks.Weseektoreducelong-termcareriskbyfocusingonthesaleofshortdurationpoliciesanduseofreinsurance.

Wesignificantlyreducedourlong-termcareriskthroughtheReinsuranceTransaction.Thebelowshowsourreserves,netofreinsuranceandinsuranceintangibles,asofSeptember27,2018,beforeandaftertheReinsuranceTransaction:

HighQualityInvestmentPortfolio

Ourinvestmentportfolioisprimarilycomprisedofhighqualityfixedmaturitysecuritieswithminimalexposuretotheequitymarkets,with$19.5billion,or82.2%,ofourinvestmentsinfixedmaturityinvestmentsandonly$40.8million,or0.2%,inequitysecuritiesatMarch31,2019.Thebalanceoftheportfolioisheldinmortgageloansandotherinvestedassets.AsofMarch31,2019,60.1%ofourfixedmaturitysecuritieswerecorporatesecurities,10.5%weremunicipalsecurities,8.8%werecommercialmortgage-backedsecuritiesand20.6%wereinotherassetclasses.Also,88.7%ofourfixedmaturityportfoliowascomprisedofinvestmentgradesecuritiesand95.7%ofourfixedmaturitieswereNAIC1or2ratedsecurities,eachasofMarch31,2019.

AsofMarch31,2019,wehad$24.4billionofinvestedassetsandcashwhichgenerated$355.8millionofnetinvestmentincomeduringthequarterendedMarch31,2019.Theinvestmentportfoliowasina$963.8millionnetunrealizedgainpositionasofMarch31,2019.

S-4

Page 14: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Inadditiontomonitoringtheoverallqualityofourinvestments,weactivelymanageinterestrateriskbymanagingthedurationsandcashflowsofourfixedmaturityinvestmentsalongwiththoseoftherelatedinsuranceliabilities.

LiquidityandCashFlow

CNOisorganizedinaholdingcompanystructure,asistypicalforinsurancecompanies.Theholdingcompanyreceivessignificantcashflowsfromitsinsurancesubsidiariesconsistingofdividends,interestpaymentsonsurplusdebenturesandadministrativeandinvestmentfees.Thenetcashflowoftheholdingcompany(excludingcapitaltransactions)was$348.8million,$341.7millionand$258.7millionin2016,2017and2018,respectively.

Theholdingcompanyhasreceivedover$200millionofdividendpaymentsfromitsinsurancesubsidiariesineachofthelastthreeyears.Inaddition,theholdingcompanyreceived$134.6million,$164.9millionand$167.1millionin2016,2017and2018,respectively,frommanagementandinvestmentfeesandinterestonsurplusdebentures.Ourconsolidatedcashflowsfurtherbenefitfromreducedcashtaxpaymentsduetosignificantnetoperatinglosscarryforwards.

Wemaychoosetoretaincapitalinourinsurancesubsidiariesortocontributeadditionalcapitaltoourinsurancesubsidiariestomaintainorstrengthentheirsurplus(whichmayberequiredtosupportthegrowthinthebusiness),andthesedecisionscouldlimittheamountavailabletopaydividendstotheholdingcompany.In2018,forexample,wemadeacapitalcontributiontoouroperatingsubsidiariesof$265.0millionrelatedtotheReinsuranceTransaction.Thiscontributionreducedourcashflowtotheholdingcompanyin2018buttheReinsuranceTransactionmeaningfullyreducedourexposuretolong-termcarebusiness.

See"—SummaryHistoricalandUnauditedProFormaConsolidatedFinancialandOperatingData"foradditionaldetail.

PositiveRatingsMomentum

CNO'sprogresshasbeenrecognizedbytheratingsagencies,withfourupgradesinaggregatesincethebeginningof2015fromMoody'sInvestorServices,Inc.("Moody's"),FitchRatings("Fitch")andA.M.BestCompany("A.M.Best").OnOctober4,2018,Moody'supgradedourissuercreditandseniordebtratingstoBaa3fromBa1,andtheoutlookfortheseratingsisstable.FollowingtheannouncementoftheReinsuranceTransaction,onAugust2,2018,Standard&Poor'sCorporation("S&P")affirmedourissuercreditandseniorcreditratingofBB+andreviseditsoutlookfortheseratingstopositivefromstable.AlsoonAugust2,2018,FitchaffirmedourissuercreditandseniordebtratingsofBB+,andrevisedtheoutlookfortheseratingstopositivefromstable.OnJanuary9,2019,A.M.Bestaffirmedourissuercreditandseniordebtratingofbbb-,andtheoutlookfortheseratingsisstable.*

Our Strategic Direction

Ourmissionistoenrichlivesbyprovidingfinancialsolutionsthathelpprotectthehealthandretirementneedsofmiddle-incomeAmericans,whilebuildingenduringvalueforallourstakeholders.Weremaincommittedtoourstrategicprioritiestogrowthefranchise,launchnewproductsandservices,expandtotherighttoreachslightlyyounger,wealthierconsumerswithinthemiddlemarket,anddeployexcesscapitaltoitshighestandbestuse.

Ourmiddle-marketfocusanddiversedistributionisakeystrengthandopportunityforCNO.WehavecareeragentsatBankersLife,wholly-ownedandindependentdistributorsatWashingtonNational

* Asecuritiesratingisnotarecommendationtobuy,sellorholdsecuritiesandmaybesubjecttorevisionorwithdrawalatanytime.

S-5

Page 15: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

andadirect-to-consumerbusinessatColonialPenntoreachconsumersaccordingtotheirpreferences.Ourproductportfoliomixiswell-alignedtotheretirement,healthcare,supplementalhealthandincomeaccumulationneedsofworking-ageconsumersaswellasthoseinandnearretirement.AsAmericanslivelongerintotheirretirementyears,consumersneedholisticretirementincomeplanning,whichincludesourinsuranceandannuitysolutions,andtheinvestmentsofferedbyourbroker-dealerandgrowingforceofregisteredinvestmentadvisors.Specifically,wearefocusedonthefollowingpriorities:

Growth

• maximizeourproductportfoliotoensureitmeetsourcustomers'needsforintegratedproductsandadvicecoveringabroadrangeoftheirfinancialgoals

• respondeffectivelytoevolvingcustomerpreferences

• expandandenhanceelementsofourbroker-dealerandregisteredinvestmentadvisorprogram

• continueour"expandtotheright"strategytoreachslightlyyoungerandwealthierconsumerswithinthemiddle-incomemarket

• increasethespeed-to-marketfornewproductsthatareagoodfitforourcustomers

• makestrategic,measuredchangestoourbusinesspracticestoimproveourcompetitiveadvantage

• continuetoinvestintechnologytosupportagentproductivityandrelationshipswithourcustomers

Increaseprofitabilityandreturnonequity

• maintainourstrongcapitalpositionandfavorablefinancialmetrics

• worktoincreaseourreturnonequity

• maintainpricingdiscipline

Effectivelymanageriskanddeploycapital

• maintainanactiveenterpriseriskmanagementprocess

• utilizeexcesscashflowtomaximizelong-termreturns

• maintainacompetitivedividendpayoutratio

Continuetoinvestintalent

• attract,retainanddevelopthebesttalenttohelpusdrivesustainablegrowth

• recruit,developandretainouragentforce

Web Benefits Design Corporation Acquisition

OnApril29,2019,weacquiredprivately-ownedWebBenefitsDesignCorporation("WBD"),aleadingonlinebenefitsadministrationfirmwithaproprietarytechnologyplatformforemployerbenefitprograms.WBDoffersafull-service,integratedemployeebenefitsadministrationsolution,distributedthroughanetworkofindependentbrokersandadirectsalesforce.Thepurchasepricewasapproximately$66millionwithanadditionalearn-outifcertainfinancialtargetsareachieved.

S-6

Page 16: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Redemption of Existing 2020 Notes

OnMay28,2019,weissuedtotheholdersofour4.500%SeniorNotesdue2020(the"Existing2020Notes")aconditionalnoticeofredemptionofall$325.0millionaggregateprincipalamountofourExisting2020NotesattheredemptionpricespecifiedintheindenturegoverningtheExisting2020Notes.TheredemptionoftheExisting2020Notesisconditioneduponthereceiptofnetproceedsfromadebtfinancingtransactioninanaggregateamountatleastequaltotheamountrequiredtopaytheredemptionprice.See"UseofProceeds."

Ourprincipalexecutiveofficesarelocatedat11825N.PennsylvaniaStreet,Carmel,Indiana46032,andourtelephonenumberatthislocationis(317)817-6100.Ourwebsiteiswww.cnoinc.com.Informationonourwebsiteisnotpartofthisprospectussupplementortheaccompanyingprospectus.OurcommonstockislistedontheNYSEunderthesymbol"CNO."

S-7

Page 17: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

THE OFFERING

Thefollowingisabriefsummaryofthetermsandconditionsofthisoffering.Itdoesnotcontainalloftheinformationthatyouneedtoconsiderinmakingyourinvestmentdecision.TounderstandallofthetermsandconditionsoftheofferingoftheNotes,youshouldcarefullyreadthisentireprospectussupplement,aswellastheaccompanyingprospectusandthedocumentsincorporatedbyreference.

S-8

Issuer CNOFinancialGroup,Inc.,aDelawarecorporation

Notesoffered$425.0millionaggregateprincipalamountofseniornotes.

Maturitydate,2029.

Interestrate%perannum.

InterestpaymentdatesInterestontheNoteswillbepaidsemi-annuallyonandofeachyear,beginningon,2020.

RankingTheNoteswillbeCNO'sseniorunsecuredobligationsandwillrankequallywithCNO'sotherseniorunsecuredandunsubordinateddebtfromtimetotimeoutstanding,includingobligationsunderourrevolvingcreditagreement.TheNoteswillbeeffectivelysubordinatedtoallofCNO'sfutureindebtednessthatissecured,totheextentofthevalueoftheassetssecuringsuchindebtedness.TheNoteswillbestructurallysubordinatedtoallexistingandfutureindebtednessandotherliabilitiesofCNO'ssubsidiaries.

AsofMarch31,2019,onanadjustedbasisaftergivingeffecttotheofferingandouruseofthenetproceedstherefromasdescribedunder"UseofProceeds,"CNOwouldhavehad$925.0millioninaggregateprincipalamountoftotalindebtedness,noneofwhichwouldhavebeensecuredandallofwhichwouldhaverankedequallyinrightofpaymentwiththeNotes.Inaddition,asofMarch31,2019,CNO'ssubsidiarieshad$25.9billionofinvestmentborrowings,policyholderobligationsandotherliabilities(excludingintercompanyliabilities),allofwhichwouldbestructurallyseniortotheNotes.

OptionalRedemptionPriorto,2029,wemayredeemtheNotes,inwholeorinpart,atanytimeorfromtimetotime,ataredemptionpriceequaltothegreaterof:

• 100%oftheprincipalamountoftheNotesbeingredeemed;or

• thesumofthepresentvaluesoftheremainingscheduledpaymentsofprincipalandinterestontheNotestoberedeemed(exclusiveofinterestaccruedto,butnotincluding,thedateofredemption)discountedtothedateofredemptiononasemi-annualbasis(assuminga360-dayyearconsistingoftwelve30-daymonths)atarateequaltothesumoftheTreasuryRate(asdefinedinthe"DescriptionofNotes")plusbasispoints,

Page 18: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

S-9

plusaccruedandunpaidinterestto,butnotincluding,theredemptiondate.Onorafter,2029,wemayredeemtheNotes,inwholeorinpart,atanytimeorfromtimetotime,ataredemptionpriceequalto100%oftheprincipalamountoftheNotestoberedeemed,plusaccruedandunpaidinterestto,butnotincluding,theredemptiondate.See"DescriptionofNotes—OptionalRedemption."

RepurchaseattheOptionoftheHoldersUponChangeofControlRepurchaseEvent

IfCNOexperiencesaChangeofControlRepurchaseEvent(asdefinedinthe"DescriptionofNotes"),CNOwillberequiredtomakeanoffertorepurchasetheNotesatapriceequalto101%oftheprincipalamountthereof,plusaccruedandunpaidinterestto,butnotincluding,thedateofsuchrepurchase.IntheeventthattheNotesreceiveinvestmentgradecreditratings,thiscovenantwillceasetoapply.See"DescriptionofNotes—RepurchaseattheOptionofHoldersChangeofControlRepurchaseEvent"and"DescriptionofNotes—CertainCovenants."

CertainCovenants

TheindenturethatwillgoverntheNotes(the"Indenture")willcontaincovenantsforyourbenefit.Thesecovenantswillrestrictourability,withcertainexceptions,to:

• createliens;

• disposeofcapitalstockofcertainsubsidiaries;and

• consolidateormergewithorintoothercompaniesortransferallorsubstantiallyallofourassets.

Thesecovenantswillbesubjecttoanumberofimportantqualificationsandexceptions.See"DescriptionofNotes."

NoListing;NoPriorMarket

CNOdoesnotintendtolisttheNotesonasecuritiesexchangeorquotethemonanautomateddealerquotationsystem.TheNotesareanewissueofsecuritiesandthereiscurrentlynoestablishedtradingmarketfortheNotes.AnactiveorliquidmarketmaynotdevelopfortheNotes.

AdditionalNotes

CNOmay,withoutnoticetoorconsentoftheholdersoftheNotes,createandissuefurthernotesrankingequallyandratablyinallrespectswiththeNotes,sothatsuchfurthernoteswillbeconsolidatedandformasingleserieswiththeNotesandwillhavethesametermsastostatus,redemptionorotherwiseastheNotes.

UseofProceeds

Weestimatethatthenetproceedsfromthisoffering,afterdeductingtheunderwriters'discountsandestimatedofferingexpensespayablebyus,willbeapproximately$420.0million.

Page 19: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

S-10

Weintendtousethenetproceedsfromthisoffering,togetherwithcashonhand,(i)toredeemouroutstandingExisting2020Notes,(ii)torepayamountsoutstandingunderourrevolvingcreditfacility(the"RevolvingCreditFacility"),and(iii)topayfeesandexpensesrelatedtothisoffering.See"UseofProceeds."

RiskFactorsYoushouldcarefullyconsiderallinformationin,orincorporatedbyreferenceinto,thisprospectussupplement.Inparticular,youshouldevaluatethespecificrisksdescribedinthesectionentitled"RiskFactors"inthisprospectussupplementforadiscussionofrisksrelatingtoaninvestmentintheNotes.PleasereadthatsectioncarefullybeforeyoudecidewhethertoinvestintheNotes.

Page 20: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Summary Historical and Unaudited Pro Forma Consolidated Financial and Operating Data

ThefollowingtablesetsforthsummaryhistoricalandunauditedproformaconsolidatedfinancialandoperatingdataforCNOFinancialGroup,Inc.asofthedatesandfortheperiodsindicated.Wehavepreparedthesummaryhistoricalfinancialandoperatingdata,otherthanstatutorydata,inconformitywithGAAP(the"GAAPData").WehavederivedthesummaryGAAPData:(i)asofDecember31,2018and2017andforthethreeyearsendedDecember31,2018fromourauditedconsolidatedfinancialstatementsincorporatedbyreferenceintothisprospectussupplement,(ii)asofDecember31,2016fromourauditedconsolidatedfinancialstatementsnotincludedinthisprospectussupplement,(iii)asofMarch31,2019andforthethreemonthsendedMarch31,2019andMarch31,2018fromourunauditedconsolidatedfinancialstatementsincorporatedbyreferenceintothisprospectussupplementand(iv)asofMarch31,2018fromourunauditedconsolidatedfinancialstatementsnotincludedinthisprospectussupplement.

TheunauditedproformacondensedconsolidatedfinancialdataforthetwelvemonthsendedMarch31,2019wasderivedfromourunauditedproformacondensedconsolidatedfinancialstatementscontainedinourCurrentReportonForm8-KfiledonMay28,2019,incorporatedbyreferenceintothisprospectussupplementandtheproformaadjustmentsgiveeffecttoeventsthataredirectlyattributabletotheReinsuranceTransactionasiftheReinsuranceTransactionoccurredbeforeJanuary1,2018.TheunauditedproformacondensedconsolidatedfinancialdataispresentedbasedoninformationavailableuponclosingoftheReinsuranceTransactionandisnotreflectiveofourresultsofoperationsduringthetwelvemonthsendedMarch31,2019hadtheReinsurancetransactionoccurredbeforeJanuary1,2018.Additionally,theunauditedproformacondensedconsolidatedfinancialdatadoesnotreflectfutureeventsthatarenotdirectlyattributabletotheReinsuranceTransaction.Actualresultsduringfutureperiodsmayvarysignificantlyfromtheresultsreflectedintheunauditedproformacondensedconsolidatedfinancialdataincludedherein.

Intheopinionofmanagement,theunauditedfinancialdataforinterimperiodsreflectalladjustments,consistingonlyofnormalandrecurringadjustments,necessaryforafairpresentationoftheresultsforthoseperiods.Operatingresultsforinterimperiodsarenotnecessarilyindicativeoftheresultsthatmaybeexpectedfortheentirefiscalyear.

ThehistoricalandproformadataforthetwelvemonthsendedMarch31,2019havebeenderivedbysubtractingthedataforthethreemonthsendedMarch31,2018fromthedatafortheyearendedDecember31,2018,andaddingthecorrespondingdataforthethreemonthsendedMarch31,2019.WeconsidertheunauditedproformafinancialresultsforthetwelvemonthsendedMarch31,2019tobemorerepresentativeofourcurrentoperationsthanthefinancialresultsforthefiscalyearendedDecember31,2018,sincetheunauditedproformafinancialresultsforthetwelvemonthsendedMarch31,2019reflecttheproformaimpactsoftheReinsuranceTransactionforthemostrecentlycompletedtwelvemonthperiod.

Wehavederivedthestatutorydatafromthestatementsfiledbyourinsurancesubsidiarieswithregulatoryauthoritiesandhavepreparedthestatutorydatainaccordancewithstatutoryaccountingpractices,whichvaryincertainrespectsfromGAAP.

TheasadjustednetoperatingincomeforthetwelvemonthsendedMarch31,2019giveseffecttothisofferingandouruseofproceedstherefromasifthisofferinghadoccurredonApril1,2018andtheasadjusteddebttototalcapitalratio(excludingaccumulatedothercomprehensiveincome)asofMarch31,2019giveseffecttothisofferingandouruseofproceedstherefromasifthisofferinghadoccurredonMarch31,2019.

Thedatashouldbereadinconjunctionwiththesectionsentitled"PresentationofFinancialData;Non-GAAPFinancialMeasures,""UseofProceeds"and"Capitalization"includedinthisprospectussupplementaswellastheinformationsetforthunder"Management'sDiscussionandAnalysisof

S-11

Page 21: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

ConsolidatedFinancialConditionandResultsofOperations"incorporatedbyreferencefromourQuarterlyReportonForm10-QforthequarterendedMarch31,2019andourAnnualReportonForm10-KfortheyearendedDecember31,2018andourconsolidatedfinancialstatementsandrelatednotesincorporatedbyreferenceintothisprospectussupplement.

S-12

Pro Forma Twelve Months Ended

March 31, 2019

Three Months Ended

March 31,

Twelve Months Ended

March 31, 2019

Year Ended December 31,

2016 2017 2018 2018 2019 (dollars in millions) StatementofOperationsData:

Insurancepolicyincome $ 2,601.1 $ 2,647.3 $ 2,593.1 $ 659.9 $ 619.5 $ 2,552.5 $ 2,465.1Netinvestmentincome 1,325.2 1,551.3 1,306.2 341.9 355.8 1,320.1 1,225.0Netrealizedinvestmentgains(losses) 8.3 50.3 352.1 (15.2) 16.1 383.4 18.5

Totalrevenues 3,985.1 4,297.2 4,313.5 1,007.8 1,023.0 4,328.7 3,791.3Interestexpense 116.4 123.7 149.8 33.6 41.0 157.2 157.2Totalbenefitsandexpenses 3,631.9 3,816.7 4,578.3 899.7 957.4 4,636.0 3,406.6Income(loss)beforeincometaxes 353.2 480.5 (264.8) 108.1 65.6 (307.3) 384.7

Incometaxexpense(benefit) (5.0) 304.9 50.2 23.8 13.8 40.2 80.7Netincome(loss) 358.2 175.6 (315.0) 84.3 51.8 (347.5) 304.0

BalanceSheetData—atPeriodEnd:

Totalinvestments $ 26,237.6 $ 27,854.1 $ 22,995.4 $ 27,416.0 $ 23,679.2 Totalassets 31,975.2 33,110.3 31,439.8 32,809.1 32,314.4 Notespayable—directcorporateobligations(a) 912.9 914.6 916.8 915.1 917.3

Totalliabilities 27,488.3 28,262.8 28,068.9 28,191.9 28,476.5 Shareholders'equity 4,486.9 4,847.5 3,370.9 4,617.2 3,837.9

StatutoryData—atPeriodEnd:

Statutorycapitalandsurplus $ 1,956.8 $ 1,904.4 $ 1,652.8 $ 1,918.9 $ 1,717.4 Assetvaluationreserve 253.3 246.8 233.3 264.7 248.0 Totalstatutorycapitalandsurplusandassetvaluationreserve 2,210.1 2,151.2 1,886.1 2,183.6 1,965.4

OtherKeyMetrics: Netoperatingincome(b) $ 262.5 $ 300.9 $ 303.1 $ 73.9 $ 65.8 $ 295.0 $ 286.7AdjustedEBIT(b) 456.1 501.2 429.2 106.8 95.5 417.9 407.0Debttototalcapitalratio(excludingaccumulatedothercomprehensiveincome)(c) 19.1% 20.1% 22.3% 19.7% 22.4

Statutorynetgain(loss)fromoperationsbeforenetrealizedcapitalgains(d) $ 286.3 $ 362.2 $ (337.1) $ 51.5 $ 83.3

AggregateRBCratio(e) 459% 446% 393% 427% 416%

Page 22: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

S-13

As Adjusted Twelve Months Ended March 31, 2019

(dollars in millions) OtherKeyMetrics: Netoperatingincome(b) $ 292.5Debttototalcapitalratio(excludingaccumulatedothercomprehensiveincome)(c) 22.3%

(a) Notespayable—directcorporateobligationsconsistofindebtednessoutstandingunderourRevolvingCreditFacility,theExisting2020Notesandour5.250%SeniorNotesdue2025(the"Existing2025Notes"),lessunamortizeddebtissuancecosts.

(b) NetoperatingincomeandAdjustedEBITarenon-GAAPmeasureswhicharecalculatedassetforthbelow.

WepresentnetoperatingincomeandAdjustedEBITbecausemanagementbelievesthattheseperformancemeasuresarebetterindicatorsoftheongoingbusinessesandtrendsinourbusiness.Netoperatingincomeispresentedasearningsbefore:(i)lossonreinsurancetransaction,includingimpactoftaxes;(ii)netrealizedinvestmentgainsorlossesfromsalesandimpairments,netofrelatedamortizationandtaxes;(iii)netchangeinmarketvalueofinvestmentsrecognizedinearnings,netoftaxes;(iv)fairvaluechangesduetofluctuationsintheinterestratesusedtodiscountembeddedderivativeliabilitiesrelatedtoourfixedindexannuities,netofrelatedamortizationandtaxes;(v)fairvaluechangesandamendmentrelatedtotheagentdeferredcompensationplan,netoftaxes;(vi)lossonextinguishmentofdebt,netoftaxes;(vii)changesinthevaluationallowancefordeferredtaxassetsandothertaxitems;and(viii)othernon-operatingitemsconsistingprimarilyofearningsattributabletovariableinterestentities.Managementbelievessuchmeasureisimportanttoevaluatethefinancialperformanceofthecompany,andisakeymeasurecommonlyusedinthelifeinsuranceindustry.Managementusesthismeasuretoevaluateperformancebecausetheitemsexcludedfromnetoperatingincomecanbeaffectedbyeventsthatareunrelatedtothecompany'sunderlyingfundamentals.AdjustedEBITispresentedasnetoperatingincomeexcludingcorporateinterestexpenseandincometaxexpense.Inaddition,managementusesthesenon-GAAPfinancialmeasuresinitsbudgetingprocess,financialanalysisofsegmentperformanceandinassessingtheallocationofresources.Webelievethesenon-GAAPfinancialmeasuresenhanceaninvestor'sunderstandingofourfinancialperformanceandallowsthemtomakemoreinformedjudgmentsabouttheCompanyasawhole.Thesemeasuresalsohighlightoperatingtrendsthatmightnototherwisebeapparent.However,netoperatingincomeandAdjustedEBITarenotmeasurementsoffinancialperformanceunderGAAPandshouldnotbeconsideredasalternativestocashflowfromoperatingactivities,asmeasuresofliquidity,orasalternativestonetincomeasmeasuresofouroperatingperformanceoranyothermeasuresofperformancederivedinaccordancewithGAAP.Inaddition,netoperatingincomeandAdjustedEBITshouldnotbeconstruedasaninferencethatourfutureresultswillbeunaffectedbyunusualornon-recurringitems.NetoperatingincomeandAdjustedEBIThavelimitationsasanalyticaltools,andyoushouldnotconsidersuchmeasureseitherinisolationorassubstitutesforanalyzingourresultsasreportedunderGAAP.OurdefinitionsandcalculationofnetoperatingincomeandAdjustedEBITarenotnecessarilycomparabletoothersimilarlytitledmeasuresusedbyothercompaniesduetodifferentmethodsofcalculation.

Netoperatingincome,asadjusted,forthetwelvemonthsendedMarch31,2019adjustsforinterestexpenseforthetwelvemonthsendedMarch31,2019asifthisofferingandouruseofproceedstherefromhadoccurredonApril1,2018.

Page 23: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

S-14

ThetablebelowreconcilesAdjustedEBITandnetoperatingincometonetincome(loss),thecorrespondingGAAPmeasure:

Pro Forma Twelve Months Ended

March 31, 2019

Three Months Ended

March 31,

Twelve Months Ended

March 31, 2019

Year Ended December 31,

2016 2017 2018 2018 2019 (dollars in millions) AdjustedEBIT: BankersLife $ 375.6 $ 367.5 $ 340.6 $ 77.5 $ 63.1 $ 326.2 $ 322.8WashingtonNational 102.9 98.3 121.9 34.3 30.5 118.1 118.1ColonialPenn 1.7 22.6 14.8 (1.5) (1.4) 14.9 14.9Long-termcareinrun-off 18.4 53.1 22.9 12.0 2.5 13.4 5.9AdjustedEBITfrombusinesssegments 498.6 541.5 500.2 122.3 94.7 472.6 461.7

Corporateoperations,excludingcorporateinterestexpense (42.5) (40.3) (71.0) (15.5) 0.8 (54.7) (54.7)AdjustedEBIT 456.1 501.2 429.2 106.8 95.5 417.9 407.0

Corporateinterestexpense (45.8) (46.5) (48.0) (11.9) (12.1) (48.2) (48.2)Operatingearningsbeforetaxes 410.3 454.7 381.2 94.9 83.4 369.7 358.8

Taxexpenseonoperatingincome 147.8 153.8 78.1 21.0 17.6 74.7 72.1Netoperatingincome 262.5 300.9 303.1 73.9 65.8 295.0 286.7

Netrealizedinvestmentgains(losses)fromsalesandimpairments(netofrelatedamortization) 9.0 34.3 37.9 0.5 (0.7) 36.7 35.2

Netchangeinmarketvalueofinvestmentsrecognizedinearnings (1.4) 15.0 (48.8) (15.7) 16.6 (16.5) (16.5)

Fairvaluechangesinembeddedderivativeliabilities(netofrelatedamortization) 9.6 (2.5) 55.5 25.1 (29.6) 0.8 0.8

Fairvaluechangesandamendmentrelatedtoagentdeferredcompensationplan 3.1 (12.2) 11.9 — (5.3) 6.6 6.6

Lossrelatedtoreinsurancetransaction(1) (75.4) — (704.2) — — (704.2) —

Other (2.0) (8.8) 1.7 3.3 1.2 (0.4) (0.2)Non-operatingincome(loss)beforetaxes (57.1) 25.8 (646.0) 13.2 (17.8) (677.0) 25.9

Incometaxexpense(benefit): Onnon-operatingincome(loss) (20.0) 9.0 (135.7) 2.8 (3.8) (142.3) 5.6Valuationallowancefordeferredtaxesandothertaxitems (132.8) 142.1 107.8 — — 107.8 3.0

Netnon-operatingincome(loss) 95.7 (125.3) (618.1) 10.4 (14.0) (642.5) 17.3Netincome(loss) $ 358.2 $ 175.6 $ (315.0) $ 84.3 $ 51.8 $ (347.5) $ 304.0

(1) InSeptember2016,weterminatedthereinsuranceagreementswithBeechwoodReLtd.andrecapturedthecededbusiness.InSeptember2018,wecompletedtheReinsuranceTransaction.Bothtransactionsarefurtherdescribedinthenoteentitled"SummaryofSignificantAccountingPolicies—Reinsurance"totheconsolidatedfinancialstatementsincorporatedbyreferencefromourAnnualReportonForm10-KfortheyearendedDecember31,2018.

Page 24: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

S-15

(c) Thedebttototalcapitalratio(excludingaccumulatedothercomprehensiveincome)isanon-GAAPfinancialmeasurewhichiscalculatedassetforthbelow.Managementbelievesthisnon-GAAPfinancialmeasureisusefulbecauseitremovesthevolatilitythatarisesfromchangesinaccumulatedothercomprehensiveincome.Suchvolatilityisoftencausedbychangesintheestimatedfairvalueofourinvestmentportfolioresultingfromchangesingeneralmarketinterestratesratherthanthebusinessdecisionsmadebymanagement.However,thismeasuredoesnotreplacethecorrespondingGAAPmeasure.

Thedebttototalcapitalratio(excludingaccumulatedothercomprehensiveincome),asadjusted,asofMarch31,2019,iscalculatedasifthisofferingandouruseofproceedstherefromhadoccurredonMarch31,2019.Accordingly,notespayable—directcorporateobligationsonanasadjustedbasisasofMarch31,2019,havedecreasedby$3.6milliontoreflectanincreaseinunamortizeddebtissuancecostswiththeprincipalamountofdebtremainingthesame,andshareholders'equityhasdecreasedby$5.1milliontoreflectthelossonextinguishmentofdebt.

As of December 31, As of March 31,

As Adjusted

March 31, 2019

2016 2017 2018 2018 2019 (dollars in millions) DebttoTotalCapitalRatio: Notespayable—directcorporateobligations $ 912.9 $ 914.6 $ 916.8 $ 915.1 $ 917.3 $ 913.7

Totalshareholders'equity 4,486.9 4,847.5 3,370.9 4,617.2 3,837.9 3,832.8Totalcapital $ 5,399.8 $ 5,762.1 $ 4,287.7 $ 5,532.3 $ 4,755.2 $ 4,746.5Debttototalcapitalratio 16.9% 15.9% 21.4% 16.5% 19.3% 19.2%Debttototalcapitalratio(excludingaccumulatedothercomprehensiveincome):

Notespayable—directcorporateobligations $ 912.9 $ 914.6 $ 916.8 $ 915.1 $ 917.3 $ 913.7

Totalshareholders'equity 4,486.9 4,847.5 3,370.9 4,617.2 3,837.9 3,832.8Lessaccumulatedothercomprehensiveincome (622.4) (1,212.1) (177.7) (894.3) (654.9) (654.9)

Totalcapitalasadjusted $ 4,777.4 $ 4,550.0 $ 4,110.0 $ 4,638.0 $ 4,100.3 $ 4,091.6Debttototalcapitalratio(excludingaccumulatedothercomprehensiveincome) 19.1% 20.1% 22.3% 19.7% 22.4% 22.3%

(d) BasedonstatutoryaccountingpracticesprescribedorpermittedbyregulatoryauthoritiesforCNO'sinsurancesubsidiariesafterappropriateeliminationofintercompanyaccountsamongsuchsubsidiaries.SuchaccountingpracticesdifferfromGAAP.

(e) OurRevolvingCreditFacilityrequiresthatwemaintainanaggregateRBCratioinexcessof250%.TheaggregateRBCratioiscalculatedquarterlyasone-halfoftheratioof(a)theaggregateTotalAdjustedCapitalforCNO'sinsurancesubsidiaries(asdefinedbytheapplicableregulatorofeachofCNO'sinsurancesubsidiaries),to(b)theaggregateAuthorizedControlLevelRisk-BasedCapitalforsuchinsurancesubsidiaries(asdefinedbytheapplicableregulatorofeachofCNO'sinsurancesubsidiaries).See"BusinessofCNO—GovernmentalRegulation"inourForm10-KfortheyearendedDecember31,2018incorporatedbyreferenceherein.

Page 25: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Thetablebelowshowsthesourcesofcashandinvestmentsheldbytheholdingcompany,CNO,andtheusesforsuchcashandinvestments:

S-16

Year Ended December 31,

Twelve Months Ended

March 31, 2019

2016 2017 2018 (dollars in millions) Holding Company Cash Flows, Excluding Capital Transactions Dividendsfrominsurancesubsidiaries $ 274.3 $ 357.7 $ 213.9 $ 234.9Managementandinvestmentfees 78.6 108.1 108.9 111.4Surplusdebentureinterest 56.0 56.8 58.2 58.8Earningsoncorporateinvestments 34.1 16.6 14.6 16.0Dividendsfromnon-insurancesubsidiaries 16.5 5.8 11.0 19.0Other 7.8 6.1 7.9 24.2Holding Company Sources of Cash, Excluding Capital

Transactions 467.3 551.1 414.5 464.3Holdingcompanyexpensesandother (34.3) (62.4) (72.6) (66.9)Intercompanytaxsettlements (40.7) (31.8) (12.4) (21.8)Taxpayments — (71.3) (26.0) (6.0)Interestexpense (43.5) (43.9) (44.8) (44.9)Cash Flow to Holding Company, Excluding Capital Transactions 348.8 341.7 258.7 324.7Contributiontoinsurancesubsidiaries(a) (200.0) — (265.0) (265.0)Dividendpaymentstostockholders (54.8) (59.6) (64.8) (65.8)Sharerepurchases (206.7) (166.1) (100.9) (141.9)Net Change in Holding Company Cash (112.7) 116.0 (172.0) (148.0)Non-cashchangesininvestmentbalances (5.9) 17.0 (4.2) (0.1)Cashandinvestments,beginningofperiod 382.2 263.6 396.6 377.9Cash and Investments, End of Period $ 263.6 $ 396.6 $ 220.4 $ 229.8

(a) CNOmadecapitalcontributionsof:(i)$200.0millionin2016asaresultofthetransactioninvolvingthelong-termcarebusinessthatwasrecapturedduetotheterminationofcertainreinsuranceagreementseffectiveSeptember30,2016;and(ii)$265.0millioninSeptember2018relatedtotheReinsuranceTransaction.

Page 26: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

RISK FACTORS

YourinvestmentintheNotesinvolvesrisks.Youshouldcarefullyconsidertherisksdescribedbelow,therisksdescribedunderthe"RiskFactors"sectionofourAnnualReportonForm10-KfortheyearendedDecember31,2018,whichisincorporatedbyreferenceintothisprospectussupplement,aswellastheotherinformationincludedorincorporatedbyreferenceinthisprospectussupplement,beforemakinganinvestmentdecision.Ourbusiness,financialconditionorresultsofoperationscouldbemateriallyadverselyaffectedbyanyoftheserisks,andyoumayloseallorpartofyourinvestment.Inaddition,pleaseread"Forward-LookingStatements"inthisprospectussupplementwherewedescribeadditionaluncertaintiesassociatedwithourbusiness.Pleasenotethatadditionalrisksnotpresentlyknowntousorthatwecurrentlydeemimmaterialmayalsoimpairourbusinessandoperations.

Risks Relating to Our Indebtedness and the Notes

TheNoteswillnotbeguaranteedbyoursubsidiariesand,asaresult,theNoteswillbestructurallysubordinatedtoallliabilitiesofoursubsidiaries.

TheNoteswillnotbeguaranteedbyanyofoursubsidiariesandwillbestructurallysubordinatedtotheexistingandfutureindebtednessandotherliabilitiesofoursubsidiaries.Oursubsidiariesareseparateanddistinctlegalentities.Becauseweareaholdingcompany,ourrighttoparticipateinanydistributionofassetsofanyofoursubsidiaries,uponanysubsidiary'sliquidationorreorganizationorotherwise,issubjecttothepriorclaimsofthatsubsidiary'screditors,excepttotheextentthatwemayberecognizedasacreditorofthatsubsidiary.Theapplicableinsurancelawsofthejurisdictionwhereeachofourinsurancesubsidiariesisdomiciledwouldgovernanyproceedingsrelatingtothatinsurancesubsidiary.Theinsuranceauthorityofthatjurisdictionwouldactasaliquidatororrehabilitatorforthesubsidiary.Bothcreditorsandpolicyholdersofthesubsidiarywouldbeentitledtopaymentinfullfromthesubsidiary'sassetsbeforewe,asashareholder,wouldbeentitledtoreceiveanydistributionfromthesubsidiarywhichwemightapplytomakepaymentsofprincipalandinterestontheNotesorourotherindebtedness.

Intheeventofanydefaultbyanysubsidiaryunderanycreditarrangementorotherindebtedness,itscreditorscouldacceleratethatindebtednesssothatallamountsbecomedueandpayablepriortothatsubsidiarydistributingamountstousthatcouldhavebeenusedtomakepaymentsontheNotes.Inaddition,ifwecausedanyinsurancecompanysubsidiarytopayadividendtoustopayobligationsontheNotes,andthatdividendweredeterminedtohavebeeneithermadeinbreachoftherelevantcorporatelawsorafraudulenttransfer,holdersoftheNotesmayberequiredtoreturnthepaymenttothatsubsidiary'screditors.AsofMarch31,2019,oursubsidiarieshad$25.9billionofinvestmentborrowings,policyholderobligationsandotherliabilities(excludingintercompanyliabilities)thatwouldhavebeenstructurallyseniortotheNotes.

Accordingly,ourobligationsundertheNoteswillbestructurallysubordinatedtoallexistingandfutureindebtednessandliabilitiesofoursubsidiaries,includinginsurancepolicy-relatedliabilities,andyou,asholdersoftheNotes,shouldlookonlytoourassetsforpaymentundertheNotes.

TheNoteswillnotbesecuredandwillbesubjecttopriorclaimsofoursecuredcreditors.AnyfuturecollateralsecuringtheNotesmaynotprovideyouwithmeaningfulprotection.Ifadefaultoccurs,wemaynothavesufficientfundstofulfillourobligationsundertheNotes.

TheNoteswillnotbesecuredbyanyofourassetsandwillbeeffectivelyjuniorinrightofpaymenttotheextentoftherealizablevalueofanycollateralpledgedwithrespecttoanysecuredindebtedness.AsofMarch31,2019,onanasadjustedbasisaftergivingeffecttothisofferingandouruseofthenetproceedstherefrom,wewouldhavehad$925.0millionoftotalindebtedness,noneofwhichwouldhavebeensecuredindebtedness.TheIndenturewillpermitusandoursubsidiariesto

S-17

Page 27: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

incursecureddebtunderspecifiedcircumstances.Ourassetsandtheassetsofoursubsidiarieswillbesubjecttopriorclaimsbyanysecuredcreditors.Intheeventofourbankruptcy,liquidation,reorganization,dissolutionorotherwindingup,assetsthatsecuredebtwillbeavailabletopayobligationsontheNotesonlyafteralldebtsecuredbythoseassetshasbeenrepaidinfull.IfweincuranyadditionalobligationsthatrankequallywiththeNotes,includingtradepayables,theholdersofthoseobligationswillbeentitledtoshareratablywithyouinanyproceedsdistributeduponourbankruptcy,liquidation,reorganization,dissolutionorotherwindingup.Thismayhavetheeffectofreducingtheamountofproceedspaidtoyou.Iftherearenotsufficientassetsremainingtopayallthesecreditors,thenalloraportionoftheNotesthenoutstandingwouldremainunpaid.

OursubstantialdebtobligationscouldadverselyaffectourfinancialconditionandpreventusfromfulfillingourobligationsundertheNotes.

Wehaveasignificantamountofindebtedness.AsofMarch31,2019,onanasadjustedbasisaftergivingeffecttothisofferingandouruseofthenetproceedstherefrom,ourindebtednesswouldhavebeen$925.0million.

Subjecttothelimitscontainedinagreementsgoverningouroutstandingindebtedness,wemaybeabletoincuradditionaldebtfromtimetotimetofinanceworkingcapital,capitalexpenditures,investmentsoracquisitions,orforotherpurposes.Ifwedoso,therisksrelatedtoourhighlevelofdebtcouldintensify.OurhighlevelofdebtcouldhaveimportantconsequencestotheholdersoftheNotes,includingthefollowing:

• makingusmorevulnerabletounfavorableeconomicconditionsandareductioninourrevenues;

• makingitmoredifficultforustosatisfyourobligationswithrespecttotheNotes,theExisting2025Notes,theRevolvingCreditFacilityandourotherdebt;

• limitingourabilitytoobtainadditionalfinancingforworkingcapital,capitalexpenditures,acquisitionsandgeneralcorporatepurposes;

• requiringasubstantialportionofourcashflowstobededicatedtodebtservicepaymentsinsteadofotherpurposes;

• increasingourvulnerabilitytogeneraladverseeconomicandindustryconditions;

• limitingourflexibilityinplanningforandreactingtochangesintheindustryinwhichwecompete;

• exposingustotheriskofincreasedinterestratesundercertainofourborrowings,includingborrowingsunderourrevolvers,whichareatvariableratesofinterest;

• limitingourabilitytoborrowadditionalamountsforworkingcapital,capitalexpenditures,debtservicerequirements,executionofourgrowthstrategy,orotherpurposes,includingincurringadditionalindebtedness;

• makingitmoredifficultforustopursuestrategicacquisitions,jointventures,alliancesandcollaborations;

• placingusatadisadvantagecomparedtoother,lessleveragedcompetitors;and

• increasingourcostofborrowing.

Ourabilitytoserviceourindebtednesswilldependonourfutureperformance,whichwillbeaffectedbyprevailingeconomicconditionsandfinancial,business,regulatoryandotherfactors.Someofthesefactorsarebeyondourcontrol.Ifwecannotgeneratesufficientcashflowfromoperationstoserviceourindebtednessandtomeetourotherobligationsandcommitments,wemayberequiredtorefinanceourdebtortodisposeofassetstoobtainfundsforsuchpurpose.Wecannotassureyouthat

S-18

Page 28: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

debtrefinancingorassetdispositionscouldbecompletedonatimelybasisoronsatisfactoryterms,ifatall,orwouldbepermittedbythetermsofourdebtinstruments.

TheIndenturewillcontaincovenantsthatrestrictourandcertainofoursubsidiaries'abilitytoincurliens,disposeofcapitalstockofourinsurancesubsidiaries,orconsolidate,mergewith,orconvey,transferorleasesubstantiallyalloftheirassetsto,anotherperson,andtheindenturegoverningtheExisting2025Notesalsoincludescovenantsthatrestrictourandcertainofoursubsidiaries'abilitytoenterintosaleandleasebacktransactionsandtheabilityofcertainofoursubsidiariestoincurindebtednesswithoutalsoguaranteeingtheNotes.Ourfailuretocomplywithanyofthesecovenantscouldresultintheaccelerationofouroutstandingindebtedness.Ifaccelerationoccurs,wewouldnotbeabletorepayourdebtanditisunlikelythatwewouldbeabletoborrowsufficientadditionalfundstorefinanceourdebt.Evenifnewfinancingismadeavailabletous,itmaynotbeavailableonacceptableorreasonableterms.Anaccelerationofourindebtednesswouldimpairourabilitytooperateasagoingconcern.

Weandoursubsidiariesmaybeabletoincursubstantialadditionaldebt.Thiscouldfurtherexacerbatetherisksassociatedwithourcurrentdebtlevels.

Weandoursubsidiariesmaybeabletoincursubstantialadditionalindebtednessinthefuture.ThetermsoftheIndentureandourotheragreementsgoverningourdebtdonotprohibitusoroursubsidiariesfromincurringadditionaldebt.Ifnewdebtisaddedtoourandoursubsidiaries'currentdebtlevels,therelatedrisksthatweandtheynowfacecouldintensifyandourabilitytosatisfyourobligationswithrespecttotheNotescouldbeadverselyaffected.

Toserviceourindebtedness,wewillrequireasignificantamountofcash.Ourabilitytogeneratecashdependsonmanyfactorsbeyondourcontrol,andanyfailuretomeetourdebtserviceobligationscouldharmourbusiness,financialconditionandresultsofoperations.

Ourabilitytomakepaymentsonandtorefinanceourindebtedness,includingtheExisting2025NotesandtheNotes,andtofundworkingcapitalneedsandplannedcapitalexpenditureswilldependonourabilitytogeneratecashinthefuture.This,toacertainextent,issubjecttogeneraleconomic,financial,competitive,business,legislative,regulatoryandotherfactorsthatarebeyondourcontrol.

Ifourbusinessdoesnotgeneratesufficientcashflowfromoperationsoriffutureborrowingsarenotavailabletousinanamountsufficienttoenableustopayourindebtedness,includingtheNotes,ortofundourotherliquidityneeds,wemayneedtorefinancealloraportionofourindebtedness,includingtheNotes,onorbeforetherespectivematuritydatesthereof,sellassets,reduceordelaycapitalinvestmentsorseektoraiseadditionalcapital,anyofwhichcouldhaveamaterialadverseeffectonouroperations.Inaddition,wemaynotbeabletocompleteanyoftheseactions,ifnecessary,oncommerciallyreasonabletermsoratall.Adownturnintheeconomywillputincreasingpressureonourrevenue,cashflowsandoperatingmarginsandconsequentlyourabilitytoserviceoursubstantialdebt.Inaddition,ourongoingrestructuringactivitieswillrequirecertaincashoutlaysthatmayputfurtherpressureonourcashflows.

Ourabilitytorestructureorrefinanceourindebtedness,includingtheNotes,willdependontheconditionofthecapitalmarketsandourfinancialconditionatsuchtime.Anyrefinancingofourdebtcouldbeathigherinterestratesandmayrequireustocomplywithmoreonerouscovenants,whichcouldfurtherrestrictourbusinessoperations.Thetermsofexistingorfuturedebtinstrumentsmaylimitorpreventusfromtakinganyoftheseactions.Inaddition,anyfailuretomakescheduledpaymentsofinterestandprincipalonouroutstandingindebtednesswouldlikelyresultinareductionofourcreditrating,whichcouldharmourabilitytoincuradditionalindebtednessoncommerciallyreasonabletermsoratall.Ourinabilitytogeneratesufficientcashflowtosatisfyourdebtserviceobligations,ortorefinanceorrestructureourobligationsoncommerciallyreasonabletermsoratall,

S-19

Page 29: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

wouldhaveanadverseeffect,whichcouldbematerial,onourbusiness,financialconditionandresultsofoperations,aswellasonourabilitytosatisfyourobligationsinrespectoftheNotes.

Inaddition,ifweareunabletomeetourdebtserviceobligationsundertheNotes,theholdersoftheNoteswouldhavetherighttocausetheentireprincipalamountofNotestobecomeimmediatelydueandpayable.Iftheamountsoutstandingundertheseinstrumentsareaccelerated,wecannotassureyouthatourassetswillbesufficienttorepayinfullthemoneyowedtoourdebtholders,includingholdersoftheNotes.

Ourfailuretocomplywiththeagreementsrelatingtoouroutstandingindebtedness,includingasaresultofeventsbeyondourcontrol,couldresultinaneventofdefaultthatcouldmateriallyandadverselyaffectourresultsofoperationsandourfinancialcondition,andwemaynotbeabletomakepaymentsontheNotes.

Anydefaultunderanyoftheagreementsrelatingtoouroutstandingindebtednessandtheremediessoughtbytheholdersofsuchindebtednesscouldpreventusfrompayingprincipal,premium,ifany,andinterestontheNotesandsubstantiallydecreasethemarketvalueoftheNotes.Additionally,theholdersofthedefaulteddebtcouldcauseallamountsoutstandingwithrespecttothatdebttobedueandpayableimmediately.Uponaccelerationofcertainofourotherindebtedness,holdersofNotescoulddeclareallamountsoutstandingundertheNotesimmediatelydueandpayable.Wecannotassureyouthatourassetsorcashflowwouldbesufficienttofullyrepayborrowingsunderouroutstandingdebtinstrumentsifaccelerateduponaneventofdefault.Further,ifweareunabletorepay,refinanceorrestructureanyofoursecuredindebtedness,theholdersofsuchdebtcouldproceedagainstthecollateralsecuringthatindebtedness.Inaddition,anyeventofdefaultordeclarationofaccelerationunderonedebtinstrumentcouldalsoresultinaneventofdefaultunderoneormoreofourotherdebtinstruments.

Federalandstatestatutesallowcourts,underspecificcircumstances,tovoidtheNotes.

Underthefederalbankruptcylawsandcomparableprovisionsofstatefraudulenttransferlaws,theNotescouldbevoided,orclaimsinrespectoftheNotescouldbesubordinatedtoallofourotherdebtsif,amongotherthings,we,atthetimeweincurredtheindebtednessevidencedbytheNotes:

• wereinsolventorrenderedinsolventbyreasonofsuchindebtedness;

• wereengagedinabusinessortransactionforwhichourremainingassetsconstitutedunreasonablysmallcapital;

• intendedtoincur,orbelievedthatwewouldincur,debtsbeyondourabilitytopaysuchdebtsastheymature.

Inaddition,anypaymentbyuspursuanttotheNotescouldbevoidedandrequiredtobereturnedtous,ortoafundforthebenefitofourcreditors.Themeasuresofinsolvencyforpurposesofthesefraudulenttransferlawswillvarydependinguponthelawappliedinanyproceedingtodeterminewhetherafraudulenttransferhasoccurred.Generally,however,wewouldbeconsideredinsolventif:

• thesumofourdebts,includingcontingentliabilities,weregreaterthanthefairsaleablevalueofallofourassets;

• ifthepresentfairsaleablevalueofourassetswerelessthantheamountthatwouldberequiredtopayourprobableliabilityonexistingdebts,includingcontingentliabilities,astheybecomeabsoluteandmature;or

• wecouldnotpayourdebtsastheybecomedue.

Althoughwebelievethatwearenotinsolvent,donothaveunreasonablysmallcapitalforthebusinessinwhichweareengagedandhavenotincurreddebtsbeyondourabilitytopaysuchdebtsas

S-20

Page 30: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

theymature,therecanbenoassuranceastowhatstandardacourtwouldapplyinmakingsuchdeterminationsorthatacourtwouldagreewithourconclusionsinthisregard.

WemaynothavesufficientfundstorepurchasetheNotesoranyofourothersecuritiesuponachangeofcontrolrepurchaseevent.

WemustoffertopurchasealltheNotesthenoutstanding,atapurchasepriceequalto101%oftheirprincipalamount,plusaccruedinterest(ifany)tothepaymentdate,upontheoccurrenceofachangeofcontrolifaratingdeclineoftheNotesoccursdirectlyasaresultofachangeofcontrolandsuchdeclineoccurswithinaspecifiedperiodoftimeafterpublicnoticeofachangeofcontrolortheintentiontoeffectachangeofcontrol.See"DescriptionoftheNotes—RepurchaseattheOptionofHoldingsChangeofControlRepurchaseEvent"foramorecompletedescriptionoftherepurchaseobligations.TherecanbenoassurancethatwewillhavesufficientfundsavailableatthetimeofanychangeofcontroltorepurchasetheNotesthatmightbeoutstanding.OurabilitytorepurchasetheNotesincashmaybelimitedbylaworthetermsofotheragreementsrelatingtoourindebtednessoutstandingatthetime.OurfailuretorepurchasetheNoteswhenrequiredwouldresultinaneventofdefaultwithrespecttotheNotes.OurinabilitytopayforyourNotesthataretenderedforrepurchasecouldresultinyourreceivingsubstantiallylessthantheprincipalamountoftheNotes.

Oneofthecircumstancesunderwhichachangeofcontrolmayoccurisuponthesaleordispositionofallorsubstantiallyallofourassets.However,thephrase"allorsubstantiallyall"willlikelybeinterpretedunderapplicablestatelawandwillbedependentuponparticularfactsandcircumstances.Asaresult,theremaybeadegreeofuncertaintyinascertainingwhetherasaleordispositionof"allorsubstantiallyall"ofourcapitalstockorassetshasoccurred,inwhichcase,theabilityofaholderoftheNotestoobtainthebenefitofanoffertorepurchaseallofaportionoftheNotesheldbysuchholdermaybeimpaired.IfwearerequiredtorepurchasetheNotespursuanttoachangeofcontrolofferwecouldrequirethird-partyfinancing.Wecannotbesurethatwewouldbeabletoobtainthird-partyfinancingonacceptabletermsoratall.

OurobligationtomakesuchachangeofcontrolofferwillbesubjecttobeingsuspendediftheNotesareratedBBB-(withastableoutlook)orbetterbyStandard&Poor'sRatingsServicesandBaa3(withastableoutlook)orbetterbyMoody'sInvestorsService,Inc.,providedthatatsuchtimenodefaultundertheIndenturehasoccurredandiscontinuing.See"DescriptionofNotes—CertainCovenants."OnOctober4,2018,Moody'sInvestorsService,Inc.upgradedourissuercreditratingandseniordebtratingtoBaa3fromBa1.TherecanbenoassurancethattheNoteswilleverberatedinvestmentgrade,orthatiftheyareratedinvestmentgrade,thattheNoteswillmaintainsuchratings.

TheNotesareanewissueofsecurities,andthetradingmarketfortheNotesmaybelimited.

TheNotesarenotcurrently,andinthefuturewillnotbe,listedonanysecuritiesexchangeorincludedinanyautomatedquotationsystem.WecannotassureyouthataliquidmarketwilldevelopfortheNotes,thatyouwillbeabletosellyourNotesataparticulartimeorthatthepricesthatyoureceivewhenyousellyourNoteswillbefavorable.TotheextenttheNotesaretraded,theymaytradeatadiscountfromtheirinitialissuepriceorprincipalamount,dependinguponmanyfactors,includingprevailinginterestrates,themarketforsimilarsecuritiesandotherfactors,includinggeneraleconomicconditionsandourfinancialcondition,performanceandprospects.Anydeclineintradingprices,regardlessofthecause,mayadverselyaffecttheliquidityandtradingmarketsfortheseNotes.Inaddition,theconditionofthefinancialmarketsandprevailinginterestrateshavefluctuatedinthepastandarelikelytofluctuateinthefuture,whichcouldhaveanadverseeffectonthemarketpriceoftheNotes.

S-21

Page 31: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

EvenifatradingmarketfortheNotesdoesdevelop,youmaynotbeabletosellyourNotesataparticulartime,ifatall,oryoumaynotbeabletoobtainthepriceyoudesireforyourNotes.TheliquidityofanymarketfortheNoteswilldependonanumberoffactors,including:

• thenumberofholdersofNotes;

• ouroperatingperformanceandfinancialcondition;

• ourperceivedbusinessprospects;

• ourcreditrating;

• themarketforsimilarsecurities;

• theinterestofsecuritiesdealersinmakingamarketintheNotes;and

• generaleconomicconditions,includingprevailinginterestrates.

Historically,themarketfornon-investmentgradedebthasbeensubjecttodisruptionsthathavecausedsubstantialvolatilityinthepricesofthesesecurities.WecannotassureyouthatthemarketfortheNoteswillbefreefromsimilardisruptions.AnysuchdisruptionscouldhaveanadverseeffectonholdersoftheNotes.

ThelimitedcovenantsintheIndenturewillnotprovideprotectionagainstsignificanteventsthatcouldadverselyimpactyourinvestmentintheNotes.

TheIndenturecontainslimitedcovenants,includingthoserestrictingourandoursubsidiaries'abilitytoincurcertainliensandconsolidate,mergewith,orconvey,transferorleasesubstantiallyalloftheirassetsto,anotherperson.Thesecovenantsaresubjecttoimportantexceptionsandqualifications.See"DescriptionofNotes—CertainCovenants."Inaddition,theIndenturedoesnot:

• requireustomaintainanyfinancialratiosorspecificlevelsofnetworth,revenues,income,cashfloworliquidity;

• limitourabilityortheabilityofoursubsidiariestoincuradditionalindebtedness;

• limitourabilitytoenterintosaleandleasebacktransactions;

• restrictourabilitytorepurchaseorprepayoursecurities;

• restrictourabilitytoengageintransactionswithaffiliates;or

• makeotherpaymentsinrespectofourcommonstockorothersecuritiesrankingjuniortotheNotes.

Asaresultoftheforegoing,whenevaluatingthetermsoftheNotes,youshouldbeawarethatthetermsoftheIndentureandtheNoteswillnotrestrictourabilitytoengagein,orotherwisebeapartyto,avarietyofcorporatetransactions,circumstancesandeventsoutsideoftheordinarycourseofbusinessthatcouldhaveanadverseimpactonyourinvestmentintheNotes.Wemayundertakematerialtransactionssuchasmergersoracquisitionsormodifyourstrategyorbusinesslines,includingthroughaddingnewbusinessesordisposingofexistingbusinesses.Inconnectionwithanysuchtransaction,wemayincurorassumeadditionalindebtedness.Totheextentweundertakesuchnon-ordinarycoursetransactions,wemayfacedifficultiesadaptingourbusinessandourmanagementresourcesmaybeinsufficient.Anyoftheforegoingcouldnegativelyaffectourfinancialratios,networth,resultsofoperationsandcashflows.

S-22

Page 32: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Adowngrade,suspensionorwithdrawaloftheratingassignedbyaratingagencytotheNotes,ifany,couldcausetheliquidityormarketvalueoftheNotestodeclinesignificantly.

Ourcreditratingsareanassessmentbyratingagenciesofourabilitytopayourdebtswhendue.Consequently,realoranticipatedchangesinourcreditratingswillgenerallyaffectthemarketvalueoftheNotes.ThesecreditratingsmaynotreflectthepotentialimpactofrisksrelatingtothestructureormarketingoftheNotes.Creditratingsarenotarecommendationtobuy,sellorholdanysecurity,andmayberevisedorwithdrawnatanytimebytheissuingorganizationinitssolediscretion.NeitherwenoranyunderwriterundertakesanyobligationtomaintaintheratingsortoadviseholdersofNotesofanychangesinratings.Eachagency'sratingshouldbeevaluatedindependentlyofanyotheragency'srating.

Inaddition,creditratingagenciescontinuallyreviewtheirratingsforthecompaniesthattheyfollow,includingus.Thecreditratingagenciesalsoevaluatetheinsuranceindustryasawholeandmaychangetheircreditratingforusbasedontheiroverallviewofourindustry.AnegativechangeinourratingcouldhaveanadverseeffectonthepriceoftheNotes.

TheNoteswillinitiallyberatedbyStandard&Poor'sRatingsServicesandMoody'sInvestorsService,Inc.Therecanbenoassurancethattheseratingswillremainforanygivenperiodoftimeorthattheseratingswillnotbeloweredorwithdrawnentirelybyaratingagencyifinthatratingagency'sjudgmentfuturecircumstancesrelatingtothebasisoftherating,suchasadversechangesinourcompany,sowarrant.

S-23

Page 33: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

USE OF PROCEEDS

Weestimatethattheaggregatenetproceedsfromthisoffering,afterdeductingtheunderwriters'discountsandestimatedofferingexpensespayablebyus,willbeapproximately$420.0million.

Weintendtousethenetproceedsfromthisoffering,togetherwithcashonhand,to:(i)redeemouroutstandingExisting2020Notes,(ii)torepayamountsoutstandingundertheRevolvingCreditFacility,and(iii)topayfeesandexpensesrelatedtothisoffering.

Thefollowingtablesetsforththeestimatedsourcesandusesofproceedsinthisoffering.Theactualamountsmaydifferatthetimeoftheconsummationofthisoffering.

Affiliatesofcertainoftheunderwritersactasagentsand/orlendersunderourRevolvingCreditFacilityandholdcertainofourExisting2020Notes,andwillreceiveaportionofthenetproceedsofthisofferinginconnectionwiththerepaymentofamountsunderourRevolvingCreditFacilityandtheredemptionoftheExisting2020Notes.See"Underwriting."

S-24

Sources Uses (dollars in millions)

Notesofferedhereby(1) $ 425.0 RedemptionofExisting2020Notes(2) $ 330.6Cashonhand 10.7 RepaymentofRevolvingCreditFacility(3) 100.1

Estimatedfeesandexpenses(4) 5.0Totalsources $ 435.7 Totaluses $ 435.7

(1) RepresentstheaggregateprincipalamountoftheNotesofferedhereby.

(2) Includes$325.0millioninaggregateprincipalamountoftheExisting2020Notes,plusaredemptionpremiumofapproximately$5.1millionand$0.5millionofaccruedandunpaidinterestto,butnotincluding,anassumedredemptiondateofJune12,2019.

(3) Consistsofpaymentof$100.0millionofborrowingsundertheRevolvingCreditFacility,plusapproximately$0.1millionofaccruedinterestonsuchborrowingsupto,butnotincluding,anassumedrepaymentdateofJune12,2019.

(4) Consistsofestimatedfeesandexpensesrelatedtothisoffering,includinglegal,accountingandadvisoryfees.Theseestimatesaresubjecttochange.Theactualfeesandexpensesincurredaspartofthisofferingmaybegreaterorlessthanourcurrentestimates.

Page 34: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

CAPITALIZATION

ThefollowingtablesetsforthCNO'scashandinvestmentsandourconsolidatedtotalcapitalizationasofMarch31,2019:

• onanactualbasis;and

• onanasadjustedbasistogiveeffecttothisofferingandtheapplicationofthenetproceedstherefromtoredeemtheExisting2020NotesandrepayouroutstandingborrowingsundertheRevolvingCreditFacility,asifeachhadoccurredonMarch31,2019.

Thistableshouldbereadinconjunctionwiththeinformationsetforthunder"UseofProceeds"and"DescriptionofOtherIndebtedness"includedinthisprospectussupplementaswellasourQuarterlyReportonForm10-QforthequarterendedMarch31,2019,incorporatedhereinbyreference.

S-25

As of March 31, 2019 Actual As Adjusted (dollars in millions) CNO'scashandinvestments(1) $ 229.8 $ 219.1Debt: RevolvingCreditAgreement(2) $ 100.0 $ —4.500%SeniorNotesdue2020(3) 325.0 —5.250%SeniorNotesdue2025 500.0 500.0Notesofferedhereby — 425.0Unamortizeddebtissuecosts (7.7) (11.3)Totaldebt 917.3 913.7

Shareholders'equity: Commonstock($0.01parvalue,8,000,000,000sharesauthorized;162,201,692sharesissuedandoutstanding) 1.6 1.6

Additionalpaid-incapital 2,952.2 2,952.2Accumulatedothercomprehensiveincome 654.9 654.9Retainedearnings(4) 229.2 224.1Totalshareholders'equity 3,837.9 3,832.8Totalcapitalization $ 4,755.2 $ 4,746.5

(1) Onanactualbasis,includes$229.8millionofcashandcashequivalents.Onanasadjustedbasis,reflectstheuseof$10.7millionofcashonhand.

(2) Onanactualbasis,wehad$150.0millionofavailabilityundertheRevolvingCreditFacilitywhichprovidedforanaggregateof$250.0millionofrevolvingcommitments.Onanasadjustedbasis,wewillhave$250.0millionofavailabilityundertheRevolvingCreditFacility.

(3) TheassumedredemptionofalloutstandingExisting2020Noteswouldresultinanafter-taxdebtextinguishmentchargeof$5.1millionifsuchrepaymentshadbeencompletedonMarch31,2019.TheExisting2020Noteswillberedeemedinfullinconnectionwiththisoffering.

(4) Onanasadjustedbasis,retainedearningsreflectsa$5.1millionreductionforthelossontheextinguishmentoftheExisting2020Notes.

Page 35: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

DESCRIPTION OF OTHER INDEBTEDNESS

Revolving Credit Facility

OnMay19,2015,weenteredintoa$150.0millionfour-yearunsecuredrevolvingcreditagreement(the"RevolvingCreditAgreement")withKeyBankNationalAssociation,asadministrativeagent(the"Agent"),andthelendersfromtimetotimepartythereto.OnOctober13,2017,weamendedtheRevolvingCreditAgreementtoincreasethetotalcommitmentsavailableundertheRevolvingCreditFacilityfrom$150.0millionto$250.0million,increasetheaggregateamountofadditionalincrementalloanstheCompanymayincurfrom$50.0millionto$100.0million,andextendedthematuritydateoftheRevolvingCreditFacilityfromMay19,2019totheearlierofOctober13,2022andthedatethatissixmonthspriortothematuritydateoftheExisting2020Notes,whichisNovember30,2019.

TheinterestrateswithrespecttoloansundertheRevolvingCreditAgreementarebasedon,attheCompany'soption,afloatingbaserate(definedasaperannumrateequaltothehighestof:(i)thefederalfundsrateplus0.50%;(ii)the"primerate"oftheAgent;and(iii)theeurodollarrateforaone-monthinterestperiodplusanapplicablemarginbasedontheCompany'sunsecureddebtrating),oraeurodollarrateplusanapplicablemarginbasedontheCompany'sunsecureddebtrating.ThemarginsundertheRevolvingCreditAgreementrangefrom1.375percentto2.125percent,inthecaseofloansattheeurodollarrate,and0.375percentto1.125percent,inthecaseofloansatthebaserate.AtMarch31,2019,theinterestrateontheamountsoutstandingundertheRevolvingCreditAgreementwas4.12percent.Inaddition,thedailyaverageundrawnportionoftheRevolvingCreditAgreementaccruesacommitmentfeepayablequarterlyinarrears.Theapplicablemarginfor,andthecommitmentfeeapplicableto,theRevolvingCreditAgreement,isadjustedfromtimetotimepursuanttoaratings-basedpricinggrid.

TheRevolvingCreditAgreementcontainscertainfinancial,affirmativeandnegativecovenants.ThenegativecovenantsintheRevolvingCreditAgreementincluderestrictionsthatrelateto,amongotherthingsandsubjecttocustomarybaskets,exceptionsandlimitationsforfacilitiesofthistype:(i)subsidiarydebt;(ii)liens;(iii)restrictiveagreements;(iv)restrictedpaymentsduringthecontinuanceofaneventofdefault;(v)dispositionofassetsandsaleandleasebacktransactions;(vi)transactionswithaffiliates;(vii)changeinbusiness;(viii)fundamentalchanges;(ix)modificationofcertainagreements;and(x)changestofiscalyear.

TheRevolvingCreditAgreementrequirestheCompanytomaintain(eachascalculatedinaccordancewiththeRevolvingCreditAgreement):(i)adebttototalcapitalizationratioofnotmorethan35.0percent(suchratiowas22.8percentatMarch31,2019);(ii)anaggregateratiooftotaladjustedcapitaltocompanyactionlevelrisk-basedcapitalfortheCompany'sinsurancesubsidiariesofnotlessthan250percent(suchratiowasapproximately416percentatMarch31,2019);and(iii)aminimumconsolidatednetworthofnotlessthanthesumof(x)$2,674millionplus(y)50.0percentofthenetequityproceedsreceivedbytheCompanyfromtheissuanceandsaleofequityinterestsintheCompany(theCompany'sconsolidatednetworthwas$3,183.0millionatMarch31,2019,comparedtotheminimumrequirementof$2,688.8million).

TheRevolvingCreditAgreementprovidesforcustomaryeventsofdefault(subjectincertaincasestocustomarygraceandcureperiods),whichinclude,withoutlimitation,thefollowing:(i)non-payment;(ii)breachofrepresentations,warrantiesorcovenants;(iii)cross-defaultandcross-acceleration;(iv)bankruptcyandinsolvencyevents;(v)judgmentdefaults;(vi)actualorassertedinvalidityofdocumentationwithrespecttotheRevolvingCreditAgreement;(vii)changeofcontrol;and(viii)customaryERISAdefaults.

IfaneventofdefaultundertheRevolvingCreditAgreementoccursandiscontinuing,theAgentmayacceleratetheamountsandterminateallcommitmentsoutstandingundertheRevolvingCreditAgreement.

S-26

Page 36: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

WeintendtousetouseaportionofthenetproceedsfromthisofferingtorepayamountsoutstandingundertheRevolvingCreditFacility.AsofMarch31,2019,onanasadjustedbasisaftergivingeffecttothisofferingandtheuseofproceedstherefrom,wewillhave$250.0millionofavailabilityundertheRevolvingCreditFacility.

Existing 2020 Notes and Existing 2025 Notes

OnMay19,2015,theCompanyexecutedtheIndenture,datedasofMay19,2015(the"ExistingBaseIndenture")andtheFirstSupplementalIndenture,datedasofMay19,2015(togetherwiththeExistingBaseIndenture,the"ExistingIndenture"),betweentheCompanyandWilmingtonTrust,NationalAssociation,astrustee("Wilmington"),pursuanttowhichtheCompanyissued$325.0millionaggregateprincipalamountoftheExisting2020Notesand$500.0millionaggregateprincipalamountoftheExisting2025Notes(togetherwiththeExisting2020Notes,the"ExistingNotes").

TheExisting2020NotesmatureonMay30,2020,andtheExisting2025NotesmatureonMay30,2025.InterestontheExisting2020Notesispayableat4.500%perannum.InterestontheExisting2025Notesispayableat5.250%perannum.InterestontheExistingNotesispayablesemi-annuallyincashinarrearsonMay30andNovember30ofeachyear,commencingonNovember30,2015.

TheExistingNotesaretheCompany'sseniorunsecuredobligationsandrankequallywiththeCompany'sotherseniorunsecuredandunsubordinateddebtfromtimetotimeoutstanding,includingobligationsundertheRevolvingCreditAgreement.TheExistingNotesareeffectivelysubordinatedtoalloftheCompany'sfuturesecuredindebtednesstotheextentofthevalueoftheassetssecuringsuchindebtedness.TheExistingNotesarestructurallysubordinatedtoallexistingandfutureindebtednessandotherliabilitiesoftheCompany'ssubsidiaries.

TheCompanymayredeemsomeoralloftheExisting2020Notesatanytimeorfromtimetotimeata"make-whole"redemptionpriceplusaccruedandunpaidinterestto,butnotincluding,theredemptiondate.See"—RedemptionofExisting2020Notes"below.

PriortoFebruary28,2025,theCompanymayredeemsomeoralloftheExisting2025Notesatanytimeorfromtimetotimeata"make-whole"redemptionpriceplusaccruedandunpaidinterestto,butnotincluding,theredemptiondate.OnandafterFebruary28,2025,theCompanymayredeemsomeoralloftheExisting2025Notesatanytimeorfromtimetotimeataredemptionpriceequalto100%oftheprincipalamountthereofplusaccruedandunpaidinterestto,butnotincluding,theredemptiondate.

UpontheoccurrenceofaChangeofControlRepurchaseEvent(asdefinedintheExistingIndenture),theCompanywillberequiredtomakeanoffertorepurchasetheNotesatapriceequalto101%oftheprincipalamountthereof,plusaccruedandunpaidinterest,ifany,to,butnotincluding,thedateofrepurchase.

TheExistingIndenturecontainscovenantsthatrestricttheCompany'sability,withcertainexceptions,to:(i)incurcertainsubsidiaryindebtednesswithoutalsoguaranteeingtheExistingNotes;(ii)createliens;(iii)enterintosaleandleasebacktransactions;(iv)issue,sell,transferorotherwisedisposeofanysharesofcapitalstockofanyInsuranceSubsidiary(asdefinedintheExistingIndenture);and(v)consolidateormergewithorintoothercompaniesortransferallorsubstantiallyalloftheCompany'sassets.

TheExistingIndentureprovidesforcustomaryeventsofdefault(subjectincertaincasestocustomarygraceandcureperiods),whichincludenonpayment,breachofcovenantsintheExistingIndenture,failuretopayatmaturityoraccelerationofotherindebtedness,afailuretopaycertainjudgmentsandcertaineventsofbankruptcyandinsolvency.Generally,ifaneventofdefaultoccurs,Wilmingtonorholdersofatleast25%inprincipalamountofthethenoutstandingExistingNotesmay

S-27

Page 37: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

declaretheprincipalofandaccruedbutunpaidinterest,includinganyadditionalinterest,onalloftheExistingNotestobedueandpayable.

RedemptionofExisting2020Notes

WeintendtousetouseaportionofthenetproceedsfromthisofferingtoredeemalloftheoutstandingExisting2020Notes.OnMay28,2019,weissuedtotheholdersoftheExisting2020Notesaconditionalnoticeofredemptionofall$325.0millionaggregateprincipalamountoftheExisting2020Notesataredemptionpriceequaltothegreaterof(i)100%oftheprincipalamountoftheExisting2020Notesand(ii)thepresentvalueoftheRemainingScheduledPayments(asdefinedintheExistingIndenture)ontheExisting2020Notes,discountedtothedateofredemption,onasemiannualbasis,attheTreasuryRate(asdefinedintheExistingIndenture)plus50basispoints,plusaccruedandunpaidinterestto,butnotincluding,theredemptiondate.TheredemptionoftheExisting2020Notesisconditioneduponthereceiptofnetproceedsfromadebtfinancingtransactioninanaggregateamountatleastequaltotheamountrequiredtopaytheredemptionprice.

S-28

Page 38: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

DESCRIPTION OF NOTES

CNOFinancialGroup,Inc.(the"Company")willissuetheNotes(asdefinedbelow)underanindenturedated,2019,betweenitselfandU.S.BankNationalAssociation,anationalbankingassociation,astrustee(the"BaseIndenture"),assupplementedbyasupplementalindenture(the"SupplementalIndenture"and,togetherwiththeBaseIndenture,the"Indenture"),betweenitselfandU.S.BankNationalAssociation,astrusteeoftheNotes(the"Trustee").ThetermsoftheNotesincludethoseexpresslysetforthintheIndentureandthosemadepartoftheIndenturebyreferencetotheTrustIndentureActof1939,asamended(the"TrustIndentureAct").

ThisdescriptionofNotesisintendedtobeanoverviewofthematerialprovisionsoftheNotesandtheIndenture.SincethisdescriptionofNotesisonlyasummary,youshouldrefertotheIndentureforacompletedescriptionoftheobligationsoftheCompanyandyourrights.AcopyoftheIndentureisavailableuponrequestfromtheCompany.

Thedefinitionsofcertaincapitalizedtermsusedinthefollowingsummaryaresetforthbelowunder"—CertainDefinitions."Whenusedinthissection,theterms"CNO,""theCompany""we,""our"and"us"refersolelytoCNOFinancialGroup,Inc.andnottoitsSubsidiaries.

General

TheinitialofferingoftheNoteswillbefor$425,000,000inaggregateprincipalamountof%seniornotesdue2029(the"Notes").WemayissueanunlimitedprincipalamountofadditionalnoteshavingidenticaltermsandconditionsastheNotes(the"AdditionalNotes"),providedthatanysuchAdditionalNotesthatarenotfungiblewiththeNoteswearecurrentlyofferingforUnitedStatesfederalincometaxpurposeswillbeissuedwithadifferentCUSIPNumberthantheCUSIPNumberissuedwithrespecttotheNoteswearecurrentlyoffering.AnyAdditionalNoteswillbepartofthesameissueastheNotesthatwearecurrentlyofferingandwillvoteonallmatterswiththeholdersoftheNotes.TheNotes(andanyAdditionalNotes)willconstituteaseriesofdebtsecuritiesundertheBaseIndenture.WemayissueanunlimitedamountofotherseriesofdebtsecuritiesundertheBaseIndenture.

Principal, Maturity and Interest

InterestontheNoteswillbepayableat%perannum.InterestontheNoteswillbepayablesemi-annuallyincashinarrearsonandofeachyear,commencingon,2020.TheCompanywillmakeeachinterestpaymenttotheHoldersofrecordoftheNotesontheimmediatelyprecedingand.InterestontheNoteswillaccruefromthemostrecentdatetowhichinteresthasbeenpaidor,ifnointeresthasbeenpaid,fromandincludingtheIssueDate.Interestwillbecomputedonthebasisofa360-dayyearcomprisedoftwelve30-daymonths.

Principalofandpremium,ifany,andinterestontheNoteswillbepayable,andtheNoteswillbeexchangeableandtransferable,attheofficeoragencyoftheCompanymaintainedforsuchpurposes,which,initially,willbethecorporatetrustofficeoftheTrusteelocatedat100WallStreet,Suite1600,NewYorkNY10005;provided,however,thatpaymentofinterestmaybemadeattheoptionoftheCompanybycheckmailedtothePersonentitledtheretoasshownonthesecurityregister.TheNoteswillbeissuedonlyinfullyregisteredformwithoutcoupons,inminimumdenominationsof$2,000andanyintegralmultipleof$1,000inexcessthereof.Noservicechargewillbemadeforanyregistrationoftransfer,exchangeorredemptionofNotes,exceptincertaincircumstancesforanytaxorothergovernmentalchargethatmaybeimposedinconnectiontherewith.

S-29

Page 39: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Ranking

TheNoteswillbegeneralunsecuredobligationsoftheCompany.Asaresult,theNoteswillrank:

• equallyinrightofpaymentwithallexistingandfutureseniorandunsubordinatedindebtednessoftheCompany,includingobligationsunderourRevolvingCreditAgreement;

• seniorinrightofpaymenttoallfutureindebtednessoftheCompanythatisbyitstermsexpresslysubordinatedtotheNotes,ifany;

• beeffectivelysubordinatedtoallfuturesecuredindebtednessoftheCompanytotheextentofthevalueoftheassetssecuringsuchindebtedness;and

• bestructurallysubordinatedtoanyindebtednessorobligationsofourSubsidiaries.

AsofMarch31,2019,onanasadjustedbasisaftergivingeffecttothisoffering:

• theCompanywouldhavehad$925.0millioninaggregateprincipalamountoftotalIndebtedness,noneofwhichwouldhavebeensecuredindebtednessthatwouldhavebeeneffectivelyseniortotheNotes;and

• ourSubsidiarieswouldhavehadapproximately$25.9billionofinvestmentborrowings,policyholderobligationsandotherliabilities(excludingintercompanyliabilities)thatwouldhavebeenstructurallyseniortotheNotes.

OntheIssueDate,theNoteswillnotbeGuaranteedbyanySubsidiaryoftheCompany.TheNoteswillbestructurallysubordinatedtoallliabilitiesandobligationsofourSubsidiaries.ClaimsofcreditorsofourSubsidiaries,includingtradecreditors,securedcreditorsandcreditorsholdingdebtandguaranteesissuedbythoseSubsidiaries,claimsofpolicyholdersandclaimsofpreferredstockholders(ifany)ofourSubsidiariesgenerallywillhaveprioritywithrespecttotheassetsandearningsofthoseSubsidiariesovertheclaimsofcreditorsoftheCompany,includingHoldersoftheNotes.See"RiskFactors—RisksRelatingtoOurIndebtednessandtheNotes—TheNoteswillnotbeguaranteedbyoursubsidiariesand,asaresult,theNoteswillbestructurallysubordinatedtoallliabilitiesofoursubsidiaries."

Sinking Fund

TherearenomandatorysinkingfundpaymentobligationswithrespecttotheNotes.

Optional Redemption

Priorto,2029(threemonthspriorthematuritydateoftheNotes),wemayredeemtheNotesinwholeatanytimeorinpartfromtimetotime,atouroption,onatleast15butnotmorethan60dayspriornotice,ataredemptionpriceequaltothegreaterof(i)100%oftheprincipalamountoftheNotesbeingredeemedand(ii)thepresentvalueoftheRemainingScheduledPaymentsontheNotesbeingredeemedontheredemptiondate,discountedtothedateofredemption,onasemiannualbasis,attheTreasuryRateplusbasispoints,plusaccruedandunpaidinterestonsuchNotesbeingredeemedto,butnotincluding,theredemptiondate.Onorafter,2029(threemonthspriorthematuritydateoftheNotes),wemayonanyoneormoreoccasionsredeemallorapartoftheNotes,atouroption,onatleast15butnotmorethan60dayspriornotice,ataredemptionpriceequalto100%oftheprincipalamountoftheNotesbeingredeemed,plusaccruedandunpaidinterestonsuchNotesbeingredeemedto,butnotincluding,theredemptiondate.

Ifanoptionalredemptiondateisonorafteraninterestrecorddateandonorbeforetherelatedinterestpaymentdate,anyaccruedandunpaidinterestwillbepaidtothePersoninwhosenametheNoteisregisteredatthecloseofbusinessonsuchrecorddate.

S-30

Page 40: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Indeterminingtheredemptionpriceandaccruedinterest,interestshallbecalculatedonthebasisofa360-dayyearconsistingoftwelve30-daymonths.

Unlesswedefaultinpaymentoftheredemptionprice,onandaftertheredemptiondateinterestwillceasetoaccrueontheNotesorportionsoftheNotescalledforredemptionandthoseNoteswillceasetobeoutstanding.

"ComparableTreasuryIssue"meanstheUnitedStatesTreasurysecurityselectedbyanIndependentInvestmentBankerashavingamaturitycomparabletotheremainingtermoftheNotesthatwouldbeutilized,atthetimeofselectionandinaccordancewithcustomaryfinancialpractice,inpricingnewissuesofcorporatedebtsecuritiesofcomparablematuritytotheremainingtermofsuchNotes.

"ComparableTreasuryPrice"means,withrespecttoanyredemptiondate,(1)theaverageoftheReferenceTreasuryDealerQuotationsforsuchredemptiondate,afterexcludingthehighestandlowestsuchReferenceTreasuryDealerQuotationsor(2)ifweobtainfewerthanfoursuchReferenceTreasuryDealerQuotations,theaverageofallsuchQuotations.

"IndependentInvestmentBanker"meansGoldmanSachs&Co.LLCanditsrespectivesuccessors,and,atouroption,anotherinvestmentbankingfirmofnationalstandingselectedbyus.

"ReferenceTreasuryDealer"meansGoldmanSachs&Co.LLC,BarclaysCapitalInc.,KeyBancCapitalMarketsInc.andRBCCapitalMarkets,LLC,BofASecurities,Inc.andtheirrespectivesuccessors,and,atouroption,otherprimaryU.S.governmentsecuritiesdealersinNewYorkCityselectedbyus.

"ReferenceTreasuryDealerQuotations"means,withrespecttoeachReferenceTreasuryDealerandanyredemptiondate,theaverage,asdeterminedbyus,ofthebidandaskedpricesfortheComparableTreasuryIssue(expressedineachcaseasapercentageofitsprincipalamount)quotedinwritingtousbysuchReferenceTreasuryDealerat5:00p.m.,NewYorkCitytime,onthethirdbusinessdayprecedingsuchredemptiondate.

"RemainingScheduledPayments"means,withrespecttoanyNote,theremainingscheduledpaymentsoftheprincipalandinterestthereonthatwouldbedueaftertherelatedredemptiondatebutforsuchredemption(excludingaccruedbutunpaidinteresttotherelatedredemptiondate).

"TreasuryRate"means,withrespecttoanyredemptiondate,therateperyearequaltothesemi-annualequivalentyieldtomaturityoftheComparableTreasuryIssue,calculatedonthethirdbusinessdayprecedingsuchredemptiondate,assumingapricefortheComparableTreasuryIssue(expressedasapercentageofitsprincipalamount)equaltotheComparableTreasuryPriceforsuchredemptiondate.

TheTrusteeshallhavenoobligationtocalculateorverifythecalculationofthepresentvaluesoftheRemainingScheduledPayments,theTreasuryRateoranyaspectofsuchcalculations.

IflessthanalloftheNotesaretoberedeemedatanytime,theTrusteewillselecttheNotesforredemptionincompliancewiththerequirementsofDTC,oriftheNotesarenotheldthroughDTCorDTCprescribesnomethodofselection,onaproratabasisorbylot,inaccordancewiththeTrustee'scustomaryprocedures,subjecttoadjustmentssothatnoNoteinanunauthorizeddenominationremainsoutstandingaftersuchredemptionorpurchase;provided,however,thatnoNoteof$2,000inaggregateprincipalamountoflessshallberedeemedinpart.Noticesofredemptionwillbesentbyelectronicsubmission(forNotesheldinbook-entryform)orfirstclassmailatleast15but(exceptassetforthinthenextparagraph)notmorethan60daysbeforetheredemptiondatetoeachholderofNotestoberedeemedatitsregisteredaddress,exceptthatredemptionnoticesmaybesentmorethan60dayspriortoaredemptiondateifthenoticeisissuedinconnectionwithadefeasanceoftheNotesorasatisfactionanddischargeoftheIndenture.

S-31

Page 41: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Noticesofredemptionmay,attheCompany'sdiscretion,beconditionedonthesatisfactionofoneormoreconditions,including,butnotlimitedto,theconsummationofanacquisitionorfinancingtransactionorequityoffering.Inaddition,ifsuchredemptionissubjecttosatisfactionofoneormoreconditions,suchnoticeshallstatethat,intheCompany'sdiscretion,theredemptiondatemaybedelayeduntilsuchtimeasanyorallsuchconditionsshallbesatisfied,orsuchredemptionmaynotoccurandsuchnoticemayberescindedintheeventthatanyorallsuchconditionsshallnothavebeensatisfiedbytheredemptiondate,orbytheredemptiondatesodelayed.Inaddition,theCompany'smayprovideinsuchnoticethatpaymentoftheredemptionpriceandperformanceoftheCompany'sobligationswithrespecttosuchredemptionmaybeperformedbyanotherPerson.

IfanyNoteistoberedeemedinpartonly,thenoticeofredemptionthatrelatestothatNotewillstatetheportionoftheprincipalamountofthatNotethatistoberedeemed.AnewNoteinprincipalamountequaltotheunredeemedportionoftheoriginalNotewillbeissuedinthenameoftheholderofNotesuponcancellationoftheoriginalNoteifsuchNotesareheldinphysicalform.Notescalledforredemptionbecomedueonthedatefixedforredemption.Onandaftertheredemptiondate,interestceasestoaccrueonNotesorportionsofNotescalledforredemption.

TheCompanyanditsaffiliatesmayatanytimeandfromtimetotimepurchaseNotesintheopenmarket,bytenderoffer,negotiatedtransactionsorotherwise.

Repurchase at the Option of Holders—Change of Control Repurchase Event

IfaChangeofControlRepurchaseEventoccurs,unlesstheCompanyatsuchtimehasgivennoticeofredemptionasdescribedaboveunderthecaption"OptionalRedemption"withrespecttoalloutstandingNotesandallconditionstosuchredemptionhaveeitherbeensatisfiedorwaived,eachholderofNoteswillhavetherighttorequiretheCompanytorepurchasealloranypart(equalto$2,000oranintegralmultipleof$1,000inexcessthereof)ofthatholder'sNotespursuanttoaChangeofControlOfferonthetermssetforthintheIndenture.IntheChangeofControlOffer,theCompanywillofferapaymentincashequalto101%oftheaggregateprincipalamountofNotesrepurchased,plusaccruedandunpaidinterest,ifany,ontheNotesrepurchasedto,butnotincluding,thedateofpurchase(the"ChangeofControlPayment").

Within30daysfollowinganyChangeofControlRepurchaseEvent,unlesstheCompanyatsuchtimehasgivennoticeofredemptionasdescribedunderthecaption"OptionalRedemption"withrespecttoalloutstandingNotes,theCompanywillsendanoticetoeachholderandtheTrusteedescribingthetransactionortransactionsthatconstitutetheChangeofControlandofferingtorepurchaseallNotesonthedatespecifiedinthenotice(the"ChangeofControlPaymentDate"),whichdatewillbenoearlierthan15daysandnolaterthan60daysfromthedatesuchnoticeissent,pursuanttotheproceduresrequiredbytheIndentureanddescribedinsuchnotice.IfaChangeofControlPaymentDateisonorafteraninterestrecorddateandonorbeforetherelatedinterestpaymentdate,anyaccruedandunpaidinterestwillbepaidtothePersoninwhosenametheNoteisregisteredatthecloseofbusinessonsuchrecorddate.TheCompanywillcomplywiththerequirementsofRule14e-1undertheExchangeActandanyothersecuritieslawsandregulationsthereundertotheextentthoselawsandregulationsareapplicableinconnectionwiththerepurchaseoftheNotesasaresultofaChangeofControlRepurchaseEvent.TotheextentthattheprovisionsofanysecuritieslawsorregulationsconflictwiththeChangeofControlprovisionsoftheIndenture,theCompanywillcomplywiththeapplicablesecuritieslawsandregulationsandwillnotbedeemedtohavebreacheditsobligationsundertheChangeofControlprovisionsoftheIndenturebyvirtueofsuchcompliance.

S-32

Page 42: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

OntheChangeofControlPaymentDate,theCompanywill,totheextentlawful:

(1) acceptforpaymentallNotesorportionsofNotes(equalto$2,000oranintegralmultipleof$1,000inexcessthereof)properlytenderedandnotwithdrawnpursuanttotheChangeofControlOffer;

(2) depositwiththepayingagentanamountequaltotheChangeofControlPaymentinrespectofallNotesorportionsofNotesproperlytenderedandnotwithdrawn;and

(3) deliverorcausetobedeliveredtotheTrusteetheNotesproperlyacceptedtogetherwithanOfficer'sCertificatestatingtheaggregateprincipalamountofNotesorportionsofNotesbeingpurchasedbytheCompany.

ThepayingagentwillpromptlymailtoeachholderofNotesproperlytenderedandnotwithdrawntheChangeofControlPaymentforsuchNotes,andtheTrusteewillpromptlyauthenticateandmail(orcausetobetransferredbybookentry)toeachholderanewNoteequalinprincipalamounttoanyunpurchasedportionoftheNotessurrendered,ifany;provided,thateachsuchnewNotewillbeinaminimumprincipalamountof$2,000oranintegralmultipleof$1,000inexcessthereof.TheCompanywillpubliclyannouncetheresultsoftheChangeofControlOfferonorassoonaspracticableaftertheChangeofControlPaymentDate.

TheCompanywillnotberequiredtomakeaChangeofControlOfferwithrespecttotheNotesuponaChangeofControlRepurchaseEventif(1)athirdpartymakestheChangeofControlOfferwithrespecttosuchNotesinthemanner,atthetimesandotherwiseincompliancewiththerequirementssetforthintheIndentureapplicabletoaChangeofControlOffermadebytheCompanyandpurchasesalloftheNotesproperlytenderedandnotwithdrawnundertheChangeofControlOffer,or(2)anoticeofredemptionhasbeengivenpursuanttotheIndenturewithrespecttotheNotesasdescribedaboveunderthecaption"OptionalRedemption"atanytimepriorto30daysfollowinganyChangeofControlRepurchaseEvent,unlessanduntilthereisadefaultinpaymentoftheapplicableredemptionprice.Notwithstandinganythingtothecontrarycontainedherein,aChangeofControlOffermaybemadeinadvanceofaChangeofControlRepurchaseEvent,conditionedupontheconsummationofsuchChangeofControl,ifadefinitiveagreementisinplacefortheChangeofControlatthetimetheChangeofControlOfferismade.TheChangeofControlPaymentDatemay,attheCompany'sdiscretion,bedelayeduntilsuchtimeasanyconditionshallbesatisfied,orthatsuchChangeofControlRepurchaseEventmaynotoccurandsuchnoticemayberescindedintheeventthatsuchconditionshallnothavebeensatisfiedbytheChangeofControlPaymentDate,orbytheChangeofControlPaymentDateassodelayed.

"ChangeofControl"meanstheoccurrenceofanyofthefollowing:

(1) any"person"or"group"ofrelatedpersons(assuchtermsareusedinSections13(d)and14(d)oftheExchangeAct)becomesthebeneficialowner(asdefinedinRules13d-3and13d-5undertheExchangeAct),directlyorindirectly,ofamajorityofthetotalvotingpoweroftheVotingStockoftheCompany(oritssuccessorsbymerger,consolidationorpurchaseofallorsubstantiallyallofitsassets);

(2) thesale,assignment,lease,transfer,conveyanceorotherdisposition(otherthanbywayofmergerorconsolidation),inoneoraseriesofrelatedtransactions,ofallorsubstantiallyalloftheassetsoftheCompanyanditsSubsidiariestakenasawholetoany"person"(assuchtermisusedinSections13(d)and14(d)oftheExchangeAct)otherthanaSubsidiaryoftheCompany;or

(3) theadoptionbythestockholdersoftheCompanyofaplanorproposalfortheliquidationordissolutionoftheCompany.

S-33

Page 43: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

"ChangeofControlOffer"hasthemeaningassignedtothattermintheIndenturegoverningtheNotes.

"ChangeofControlRepurchaseEvent"meanstheoccurrenceofbothaChangeofControlandaRatingsEvent.

"InvestmentGrade"means(1)BBB-(withastableoutlook)orabove,inthecaseofS&P(oritsequivalentunderanysuccessorratingcategoriesofS&P)andBaa3(withastableoutlook)orabove,inthecaseofMoody's(oritsequivalentunderanysuccessorratingcategoriesofMoody's),or(2)theequivalentinrespectoftheRatingCategoryofanyRatingAgencies.

"Moody's"meansMoody'sInvestorsService,Inc.

"RatingAgencies"means(1)S&PandMoody'sor(2)ifS&PorMoody'sorbothofthemarenotmakingratingspubliclyavailable,anationallyrecognizedstatisticalratingorganizationwithinthemeaningofRule15c3-1(c)(2)undertheExchangeAct,asthecasemaybe,selectedbytheCompany,whichwillbesubstitutedforS&PorMoody'sorboth,asthecasemaybe.

"RatingCategory"means(1)withrespecttoS&P,anyofthefollowingcategories:AAA,AA,A,BBB,BB,B,CCC,CC,CandD(orequivalentsuccessorcategories);(ii)withrespecttoMoody's,anyofthefollowingcategories:Aaa,Aa,A,Baa,Ba,B,Caa,Ca,CandD(orequivalentsuccessorcategories);and(iii)theequivalentofanysuchcategoryofS&PorMoody'susedbyanotherRatingAgency.IndeterminingwhethertheratingoftheNoteshasdecreasedbyoneormoregradations,gradationswithinRatingCategories(+and-forS&P;1,2and3forMoody's;ortheequivalentgradationsforanotherRatingAgency)shallbetakenintoaccount(e.g.,withrespecttoS&P,adeclineinratingfromBB+toBB,aswellasfromBB-toB+,willconstituteadecreaseofonegradation).

"RatingsEvent"means(i)iftheNotesareratedbyoneorbothRatingAgenciesasInvestmentGrade,adecreaseintheratingoftheNotessothattheNotesareratedbelowInvestmentGradebybothRatingAgencies,(ii)iftheNotesareratedbelowInvestmentGradebybothRatingAgencies,adecreaseofoneormoregradations(includinggradationswithinRatingCategoriesaswellasbetweenRatingCategories)intheratingoftheNotesbybothRatingAgenciesor(iii)awithdrawaloftheratingoftheNotesbybothRatingAgencies,ineachcase,directlyasaresultofaChangeofControl;provided,however,thatsuchdecreaseorwithdrawaloccurson,orwithin30daysfollowing,theearlierof(x)theoccurrenceofaChangeofControlor(y)thedateofpublicnoticeoftheoccurrenceofaChangeofControloroftheintentionbytheCompany,orastockholderoftheCompany,asapplicable,toeffectaChangeofControl,whichperiodshallbeextendedsolongastheratingoftheNotesrelatingtotheChangeofControlasnotedbytheRatingAgencyisunderpubliclyannouncedconsiderationfordowngradebytheapplicableRatingAgency.

"S&P"meansStandard&Poor'sRatingsGroup.

TheprovisionsdescribedabovethatrequiretheCompanytomakeaChangeofControlOfferfollowingaChangeofControlRepurchaseEventwillbeapplicablewhetherornotanyotherprovisionsoftheIndentureareapplicable.ExceptasdescribedabovewithrespecttoaChangeofControlRepurchaseEvent,theIndenturedoesnotcontainprovisionsthatpermittheholdersoftheNotestorequirethattheCompanyrepurchaseorredeemtheNotesintheeventofatakeover,recapitalizationorsimilartransaction.

ThedefinitionofChangeofControlincludesaphraserelatingtothedirectorindirectsale,lease,transfer,conveyanceorotherdispositionof"allorsubstantiallyall"ofthepropertiesorassetsoftheCompanyanditsSubsidiariestakenasawhole.Althoughthereisalimitedbodyofcaselawinterpretingthephrase"substantiallyall,"thereisnopreciseestablisheddefinitionofthephraseunderapplicablelaw.Accordingly,theabilityofaholderofNotestorequiretheCompanytorepurchaseits

S-34

Page 44: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Notesasaresultofasale,lease,transfer,conveyanceorotherdispositionoflessthanalloftheassetsoftheCompanyanditsSubsidiariestakenasawholetoanotherPersonorgroupmaybeuncertain.

TheagreementsgoverningtheCompany'sotherIndebtednesscontain,andfutureagreementsmaycontain,prohibitionsofcertainevents,includingeventsthatwouldconstituteaChangeofControlandrepurchasesoforotherprepaymentsinrespectoftheNotes.TheexercisebytheholdersofNotesoftheirrighttorequiretheCompanytorepurchasetheNotesuponaChangeofControlRepurchaseEventcouldcauseadefaultundertheseotheragreements,eveniftheChangeofControlRepurchaseEventitselfdoesnot,duetothefinancialeffectofsuchrepurchasesontheCompany.IntheeventaChangeofControlRepurchaseEventoccursatatimewhentheCompanyisprohibitedfrompurchasingNotes,theCompanycouldattempttorefinancetheborrowingsthatcontainsuchprohibition.IftheCompanydoesnotrepaythoseborrowings,theCompanywillremainprohibitedfrompurchasingNotes.Inthatcase,theCompany'sfailuretopurchasetenderedNoteswouldconstituteanEventofDefaultundertheIndenturewhichcould,inturn,constituteadefaultundertheotherindebtedness.Finally,theCompany'sabilitytopaycashtotheholdersofNotesuponarepurchasemaybelimitedbytheCompany'sthenexistingfinancialresources.See"RiskFactors—RisksRelatingtoOurIndebtednessandtheNotes—WemaynothavesufficientfundstorepurchasetheNotesoranyofourothersecuritiesuponachangeofcontrolrepurchaseevent."

Ifholdersofnotlessthan90%inaggregateprincipalamountoftheoutstandingNotestenderanddonotwithdrawsuchNotesinaChangeofControlOfferandtheCompany,oranythirdpartymakingaChangeofControlOfferinlieuoftheCompanyasdescribedabove,purchasesalloftheNotesvalidlytenderedandnotwithdrawnbysuchholders,theCompanyorsuchthirdpartywillhavetheright,uponnotlessthan15normorethan60days'priornotice,givennotmorethan30daysfollowingsuchpurchasepursuanttotheChangeofControlOfferdescribedabove,toredeemallNotesthatremainoutstandingfollowingsuchpurchaseatapriceincashequaltotheChangeofControlPaymentplus,totheextentnotincludedintheChangeofControlPayment,accruedandunpaidinterest,ifany,thereon,to,butnotincluding,theredemptiondate.

Certain Covenants

SetforthbelowaresummariesofcertaincovenantsapplicabletotheNotescontainedintheIndenture.

IfonanydatefollowingtheIssueDate,(i)theNotesareratedbybothoftheRatingAgenciesasInvestmentGradeand(ii)noDefaulthasoccurredandiscontinuingundertheIndenture(theoccurrenceoftheeventsdescribedintheforegoingclauses(i)and(ii)beingcollectivelyreferredtoasa"CovenantSuspensionEvent"andthedatethereofbeingreferredtoasthe"SuspensionDate"),then,thecovenantlistedunder"—RepurchaseattheOptionofHolders—ChangeofControlRepurchaseEvent"inthis"DescriptionofNotes"sectionofthisprospectussupplementwillnolongerbeapplicabletotheNotes(the"SuspendedCovenant")untiltheoccurrenceoftheReversionDate(asdefinedbelow).

IntheeventthatCompanyanditsSubsidiariesarenotsubjecttotheSuspendedCovenantundertheIndentureforanyperiodoftimeasaresultoftheforegoing,andonanysubsequentdate(the"ReversionDate")bothoftheRatingAgencieswithdrawtheirratingoftheNotesasInvestmentGradeordowngradetheratingassignedtotheNotesbelowInvestmentGrade(ineachcase,totheextentpreviouslyratedasInvestmentGradebysuchRatingAgency),thentheCompanyandtheSubsidiarieswillthereafteragainbesubjecttotheSuspendedCovenantundertheIndenturewithrespecttofutureevents.TheperiodoftimebetweentheSuspensionDateandtheReversionDateisreferredtointhisdescriptionasthe"SuspensionPeriod."

NotwithstandingthattheSuspendedCovenantmaybereinstatedaftertheReversionDate,(1)noDefault,EventofDefaultorbreachofanykindwillbedeemedtoexistortohaveoccurredunderthe

S-35

Page 45: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

IndentureortheNoteswithrespecttotheSuspendedCovenant,andnoneoftheCompanyoranyofitsSubsidiariesshallbearanyliabilityforanyactionstakenoreventsoccurringduringtheSuspensionPeriod,oranyactionstakenatanytimepursuanttoanycontractualobligationarisingduringanySuspensionPeriod,ineachcaseasaresultofafailuretocomplywiththeSuspendedCovenantduringtheSuspensionPeriod(or,uponterminationoftheSuspensionPeriodorafterthattimebasedsolelyonanyactiontakenoreventthatoccurredduringtheSuspensionPeriod),and(2)followingaReversionDate,theCompanyandeachSubsidiarywillbepermitted,withoutcausingaDefaultorEventofDefault,tohonor,complywithorotherwiseperformanycontractualcommitmentsorobligationsarisingduringanySuspensionPeriodandtoconsummatethetransactionscontemplatedthereby.

TherecanbenoassurancethattheNoteswilleverberatedInvestmentGradeormaintainsuchrating.PromptlyfollowingtheoccurrenceofanySuspensionDateorReversionDate,theCompanyshallprovideanOfficer'sCertificatetotheTrusteeregardingsuchoccurrence.TheTrusteeshallhavenodutyto(i)monitortheratingsoftheNotes,(ii)ascertainwhetheraCovenantSuspensionEventorReversionDatehaveoccurred,or(iii)notifytheHoldersofanyoftheforegoing.

LimitationonLiens

TheCompanywillnot,norwillitpermitanyofitsSubsidiariesto,create,incurorassumeanyLien(otherthanPermittedLiens)thatsecuresanyIndebtednessonanypropertiesorassetsoftheCompanyorsuchSubsidiary,withoutsecuringtheNotes(togetherwith,attheoptionoftheCompany,anyotherIndebtednessoftheCompanyorsuchSubsidiaryrankingequallyinrightofpaymentwiththeNotes)equallyandratablywithor,attheoptionoftheCompany,priorto,suchotherIndebtednessforsolongassuchotherIndebtednessissosecured.AnyLienthatisgrantedtosecuretheNotesunderthiscovenantshallbeautomaticallyreleasedanddischargedatthesametimeasthereleaseoftheLienthatgaverisetotheobligationtosecuretheNotesunderthiscovenant.

"Lien"meansanymortgage,deedoftrust,pledge,lien,securityinterestorotherencumbrance(including,withoutlimitation,anyconditionalsaleorothertitleretentionagreementorleaseinthenaturethereof,andanyfilingoragreementtogivealienorfileafinancingstatementasadebtorundertheUniformCommercialCodeoranysimilarstatute,otherthantoreflectownershipbyathirdpartyofpropertyleasedtotheCompanyunderaleasewhichisnotinthenatureofaconditionalsaleortitleretentionagreement).

"PermittedLiens"means:

(1) LienssecuringIndebtednessonanypropertiesorassetsoftheCompanyoranySubsidiaryusedorusefulinaRelatedBusinessexistingatthetimeofitsacquisitionandLienscreatedcontemporaneouslywithorwithin270daysafter(orcreatedpursuanttofirmcommitmentfinancingarrangementsobtainedwithinthatperiod)thelaterof(a)theacquisitionorcompletionofconstructionorcompletionofreconstruction,renovation,remodeling,expansionorimprovement(each,an"improvement")ofsuchpropertiesorassetsor(y)theplacinginoperationofsuchpropertiesorassetsaftertheacquisitionorcompletionofanysuchconstructionorimprovement;

(2) LiensonpropertiesorassetsorsharesofCapitalStockorIndebtednessofaPersonexistingatthetimeitismerged,combinedoramalgamatedwithorintoorconsolidatedwith,oritsassetsorCapitalStockareacquiredby,theCompanyoranyofitsSubsidiariesoritotherwisebecomesaSubsidiaryoftheCompany;provided,however,thatineachcase(a)theIndebtednesssecuredbysuchLienwasnotincurredincontemplationofsuchmerger,combination,amalgamation,consolidation,acquisitionortransactioninwhichsuchPersonbecomesaSubsidiaryoftheCompanyand(b)suchLienextendsonlytothepropertiesor

S-36

Page 46: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

assetsorsharesofCapitalStockorIndebtednessofsuchPerson(andSubsidiariesofsuchPerson);

(3) LienssecuringIndebtednessinfavoroftheCompanyand/oroneormoreofitsSubsidiaries;

(4) Liensinfavoroforrequiredbyagovernmentalunitinanyrelevantjurisdiction,includinganydepartmentsorinstrumentalitythereof,tosecurepaymentsunderanycontractorstatute,ortosecuredebtsincurredinfinancingtheacquisitionorconstructionoforimprovementsoralterationstopropertysubjectthereto;

(5) Liensinfavorofanycustomerarisinginrespectofandnotexceedingtheamountofperformancedepositsandpartial,progress,advanceorotherpaymentsbythatcustomerforgoodsproducedorservicesrenderedtothatcustomerintheordinarycourseofbusinessandconsignmentarrangements(whetherasconsignororasconsignee)orsimilararrangementsforthesaleorpurchaseofgoodsintheordinarycourseofbusiness;

(6) LiensexistingontheIssueDate;

(7) Lienstosecureanyextension,renewal,refinancing,refundingorreplacement(orsuccessiveextensions,renewals,refinancings,refundingsorreplacements),inwholeorinpart,ofanyIndebtednesssecuredbyLiensreferredtoinclauses(1)through(6)aboveorLienscreatedinconnectionwithanyamendment,consentorwaiverrelatingtosuchIndebtedness,solongas(a)suchLienislimitedtoallorpartofsubstantiallythesamepropertyorassetswhichsecuredtheLienextended,renewed,refinanced,refundedorreplacedand(b)theamountofIndebtednesssecuredisnotincreased(otherthanbytheamountequaltoanycosts,expenses,premiums,feesorprepaymentpenaltiesincurredinconnectionwithanyextension,renewal,refinancing,refundingorreplacement);

(8) LiensinrespectofcashinconnectionwiththeoperationofcashmanagementprogramsandLiensassociatedwiththediscountingorsaleoflettersofcreditandcustomaryrightsofsetoff,banker'sLien,revocation,refundorchargebackorsimilarrightsunderdepositdisbursement,concentrationaccountagreementsorundertheUniformCommercialCodeorarisingbyoperationoflaw;

(9) LiensresultingfromthedepositoffundsorevidencesofIndebtednessintrustforthepurposeofdefeasingoreffectingasatisfactionanddischargeofanyIndebtednessoftheCompanyoranyofitsSubsidiaries,andlegalorequitableencumbrancesdeemedtoexistbyreasonofnegativepledges;

(10) LienssecuringIndebtednessnottoexceedanaggregateprincipalamountof$250.0million,asofthedatesuchIndebtednessisincurred;

(11) Liensimposedbylaw,suchascarriers',warehousemen'sandmechanic'sLiensandothersimilarLiensarisingintheordinarycourseofbusiness,LiensinconnectionwithlegalproceedingsandLiensarisingsolelybyvirtueofanystatutoryorcommonlawprovisionrelatingtobanker'sLiens,rightsofset-offorsimilarrightsandremediesastodepositaccountsorotherfundsmaintainedwithacreditordepositoryinstitution;

(12) Liensfortaxes,assessmentsorothergovernmentalchargesnotyetoverdueforaperiodofmorethan90daysorsubjecttopenaltiesfornon-paymentorwhicharebeingcontestedingoodfaithbyappropriateproceedings;

(13) Lienstosecuretheperformanceofbids,tradeorcommercialcontracts,governmentcontracts,purchase,construction,salesandservicingcontracts(includingutilitycontracts),leases,statutoryobligations,surety,stay,customs,revenueandappealbonds,performancebondsandotherobligationsofalikenature,ineachcaseintheordinarycourseofbusinessandto

S-37

Page 47: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

securelettersofcredit,Guarantees,bondsorothersuretiesgiveninconnectionwiththeforegoingorinconnectionwithworkers'compensation,unemploymentinsurance,generalinsuranceandotherinsurancelawsandoldagepensionsandorothertypesofsocialsecurityorretirementorsimilarlawsandregulations;

(14) Liensonstock,partnershiporotherequityinterestsinanyjointventureoftheCompanyoranyofitsSubsidiariesorinanySubsidiaryoftheCompanythatownsanequityinterestinajointventuretosecureIndebtednesscontributedoradvancedsolelytothatjointventure;providedthat,ineachcase,theIndebtednesssecuredbysuchLienisnotsecuredbyaLienonanyotherpropertyoftheCompanyoranySubsidiaryoftheCompany;

(15) Liensanddepositssecuringnettingservices,businesscreditcardprograms,overdraftprotectionandothertreasury,depositoryandcashmanagementservicesorincurredinconnectionwithanyautomatedclearing-housetransfersoffundsorotherfundtransferorpaymentprocessingservices;

(16) minorsurveyexceptions,groundleases,easements,rightsofway,minorencroachments,protrusions,municipalandzoningandbuildingordinancesandsimilarcharges,encumbrances,titledefectsorotherirregularities,governmentalrestrictionsontheuseofpropertyorconductofbusiness,andLiensinfavorofgovernmentalauthoritiesandpublicutilities,thatdonotmateriallyinterferewiththeordinarycourseofbusinessoftheCompanyanditsSubsidiaries,takenasawhole;

(17) Liensencumberingcustomaryinitialdepositsandmargindeposits,andotherLiensthatareincurredintheordinarycourseofbusiness,ineachcase,securingIndebtednessunderHedgingObligationsnotenteredintoforspeculativeinvestmentpurposesanddesignedtoprotecttheCompanyoranyofitsSubsidiariesfromfluctuationsininterestrates,currenciesorthepriceofcommoditiesorsecurities;

(18) leases,licenses,subleasesandsublicensesofassets(including,withoutlimitationrealpropertyandintellectualpropertyrights)thatdonotmateriallyinterferewiththeordinaryconductofbusinessoftheCompanyoranyofitsSubsidiaries;

(19) judgmentLiensnotgivingrisetoanEventofDefault,andLienssecuringappealorsuretybondsrelatedtosuchjudgment,solongasanyappropriatelegalproceedingsthatmayhavebeendulyinitiatedforthereviewofsuchjudgmenthavenotbeenfinallyterminatedortheperiodwithinwhichsuchproceedingsmaybeinitiatedhasnotexpired;

(20) LiensarisingfromUniformCommercialCodefinancingstatementfilingsregardingoperatingleasesenteredintobytheCompanyanditsSubsidiariesintheordinarycourseofbusiness;

(21) LiensonspecificitemsofinventoryorothergoodsandproceedsofanyPersonsecuringsuchPerson'sobligationsinrespectofbankers'acceptancesissuedorcreatedfortheaccountofsuchPersontofacilitatethepurchase,shipmentorstorageofsuchinventoryorothergoods;

(22) Liensinfavorofcustomsandrevenueauthoritiesarisingasamatteroflawtosecurepaymentofcustomsdutiesinconnectionwithimportationofgoods;

(23) Liensarisingoutofconditionalsale,titleretention,consignmentorsimilararrangementsforthesaleorpurchaseofgoodsenteredintobytheCompanyoranyofitsSubsidiariesintheordinarycourseofbusiness;

(24) LiensonfundsoftheCompanyoranySubsidiaryheldindepositaccountswiththirdpartyprovidersofpaymentservicessecuringcreditcardcharge-backreimbursementandsimilarcashmanagementobligationsoftheCompanyortheSubsidiaries;

S-38

Page 48: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

(25) LiensofacollectingbankarisingintheordinarycourseofbusinessunderSection4-208oftheUniformCommercialCodeineffectintherelevantjurisdictioncoveringonlytheitemsbeingcollectedupon;

(26) Liensarisingbyoperationoflaworcontractoninsurancepoliciesandtheproceedsthereoftosecurepremiumsthereunder;

(27) Liensoninsurancepoliciesandproceedsofinsurancepolicies(includingrebatesofpremiums)securingIndebtednessincurredtofinancethepaymentofpremiumsontheinsurancepoliciessubjecttosuchLiens;

(28) statutory,commonlaworcontractualLiensoflandlords;

(29) LiensonanycashearnestmoneydepositmadebytheCompanyoranySubsidiaryinconnectionwithanyletterofintentoracquisitionagreement;

(30) Liensinfavorofcreditcardprocessorsgrantedintheordinarycourseofbusiness;

(31) Lienssecuringcashmanagementobligationsincurredintheordinarycourseofbusiness;or

(32) LiensonassetsofanyInsuranceSubsidiariessecuringobligationsundertransactionsenteredintoinconnectionwithPermittedPortfolioInvestments.

AnyLienpermittedunderclauses(1)through(32)abovethatsecuresIndebtednessshallalsobepermittedtosecureanyprincipal,interest,penalties,fees,indemnifications,reimbursements(including,withoutlimitation,reimbursementobligationswithrespecttolettersofcredit),damagesandotherliabilities,andguaranteesofpaymentofsuchprincipal,interest,penalties,fees,indemnifications,reimbursements,damagesandotherliabilities,payableunderthedocumentationgoverninganyIndebtednessassociatedwithsuchIndebtedness.

LimitationonDispositionofStock

AslongasanyNotesareoutstanding,theCompanywillnot,anditwillnotpermitanySubsidiarytoissue,sell,transferorotherwisedisposeofanysharesofCapitalStockofanyInsuranceSubsidiary,oranysecuritiesconvertibleintoorexercisableorexchangeableforsharesofCapitalStockofanyInsuranceSubsidiary,orwarrants,rightsoroptionstosubscribefororpurchasesharesofCapitalStockofanyInsuranceSubsidiary,unlesssuchissuance,sale,transferorotherdispositionis:(i)foratleastfairvalue(asdeterminedbytheBoardofDirectorsoftheCompanyactingingoodfaith),(ii)totheCompanyoranywholly-ownedSubsidiaryoftheCompany,(iii)requiredbyanyregulationororderoranygovernmentalregulatoryauthorityor(iv)forthepurposeofqualifyingdirectors.

Notwithstandinganythingtothecontraryabove,theCompanymay(i)mergeorconsolidateanyofitsSubsidiaries(includinganyInsuranceSubsidiary)intoorwithanotheroftheCompany'swholly-ownedSubsidiariesand(ii)sell,transferorotherwisedisposeoftheCompany'sbusinessinaccordancewith"—Consolidation,Merger,Conveyance,TransferorLease"below.

ProvisionofFinancialInformation

TheIndenturewillprovidethattheCompanyshallfilewiththeTrusteeandtransmittoHoldersoftheNotessuchinformation,documentsandotherreports,andsuchsummariesthereof,asmayberequiredpursuanttotheTrustIndentureActatthetimeandinthemannerprovidedpursuanttosuchAct.

S-39

Page 49: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Consolidation,Merger,Conveyance,TransferorLease

TheIndentureprovidesthattheCompanymaynotmergeorconsolidatewith,orsell,convey,assign,transfer,leaseorotherwisedisposeofallorsubstantiallyallofthepropertiesorassetsofitanditsSubsidiariestakenasawhole,inoneormorerelatedtransactions,toanotherPerson,unless:

(1) (A)theCompanyisthecontinuingcorporationor(B)theentity(ifotherthantheCompany)formedbytheconsolidationorintowhichtheCompanyismergedortheentitythatacquiresallorsubstantiallyallofthepropertiesandassetsoftheCompanyisacorporation,partnership,limitedliabilitycompany,trustorotherentityorganizedandvalidlyexistingunderthelawsoftheUnitedStatesoranystatethereofortheDistrictofColumbia,andexpresslyassumes,bysupplementalindentureinformreasonablysatisfactorytotheTrustee,paymentoftheprincipalofandanypremiumandinterestonalltheNotesandtheperformanceofalltheCompany'sobligationsundertheNotesandtheIndenture;

(2) immediatelythereafter,noEventofDefault(andnoeventthat,afternoticeorlapseoftime,orboth,wouldbecomeanEventofDefault)hasoccurredandiscontinuing;and

(3) theCompanyhasdeliveredtotheTrusteeanOfficer'sCertificateandanopinionofcounselthatsuchtransactioncomplieswiththeapplicableprovisionsoftheIndenture.

ThepredecessorcompanywillbereleasedfromitsobligationsundertheIndentureandthePersonformedbyorsurvivinganysuchconsolidationormerger(ifotherthanCompany,asapplicable)ortowhichsuchsale,assignment,transfer,conveyanceorotherdispositionhasbeenmadewillsucceedto,andbesubstitutedfor,andmayexerciseeveryrightandpoweroftheCompanyundertheIndenture,but,inthecaseofaleaseofallorsubstantiallyallitsassets,thepredecessorwillnotbesoreleased.

Althoughthereisalimitedbodyofcaselawinterpretingthephrase"substantiallyall,"thereisnopreciseestablisheddefinitionofthephraseunderapplicablelaw.Accordingly,incertaincircumstancestheremaybeadegreeofuncertaintyastowhetheraparticulartransactionwouldinvolve"allorsubstantiallyall"ofthepropertyorassetsofaPerson.

This"Consolidation,Merger,Conveyance,TransferorLease"covenantwillnotapplytoanysale,assignment,transfer,conveyance,leaseorotherdispositionofassetsbetweenoramongtheCompanyanditsSubsidiaries.Clause(2)ofthefirstparagraphofthiscovenantwillnotapplyto(a)theCompanyconsolidatingwith,mergingintoorselling,assigning,transferring,conveying,leasingorotherwisedisposingofallorpartofitspropertiesandassetstooneoftheCompany'sSubsidiariesforanypurpose,(b)anySubsidiaryconsolidatingwith,mergingintoorselling,assigning,transferring,conveying,leasingorotherwisedisposingofallorpartofitspropertiesandassetstotheCompanyortoanotherSubsidiaryforanypurposeor(c)theCompanymergingwithorintoanAffiliatesolelyforthepurposeofreincorporatinginanotherjurisdiction.

Events of Default

Eachofthefollowingisan"EventofDefault":

(1) defaultinanypaymentofinterestonanyNotewhendue,andthecontinuanceofsuchdefaultfor30days;

(2) defaultinthepaymentofprincipaloforpremium,ifany,onanyNotewhendueatitsStatedMaturity,uponoptionalredemption,uponrequiredrepurchase,ifany,upondeclarationofaccelerationorotherwise;

(3) failurebytheCompanytocomplywithitsobligationsunder"CertainCovenants—Consolidation,Merger,Conveyance,TransferorLease"or,ifapplicable,"RepurchaseattheOptionofHolders—ChangeofControlRepurchaseEvent";

S-40

Page 50: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

(4) defaultintheperformance,orbreach,ofanycovenantoragreementoftheCompanycontainedintheIndentureorundertheNotesandcontinuanceofsuchdefaultorbreachforaperiodof60daysafternoticeasprovidedbelow(ineachcase,otherthanmattersthatwouldconstituteanEventofDefaultunderclauses(1)through(3)above);

(5) defaultunderanymortgage,indentureorinstrumentunderwhichthereisissuedorbywhichthereissecuredorevidencedanyIndebtednessformoneyborrowedbytheCompanyoranyofitsSubsidiaries(orthepaymentofwhichisguaranteedbytheCompanyoranyofitsSubsidiaries),otherthanIndebtednessowedtotheCompanyoraSubsidiary,whethersuchIndebtednessorGuaranteenowexists,oriscreatedaftertheIssueDate,whichdefault:

(a) iscausedbyafailuretopayprincipalonsuchIndebtednessatitsfinalstatedmaturitywithinthegraceperiodprovidedintheagreementsorinstrumentsgoverningsuchIndebtedness("paymentdefault");or

(b) resultsintheaccelerationofsuchIndebtednesspriortoitsstatedfinalmaturity(the"cross-accelerationprovision");

and,ineachcase,theprincipalamountofanysuchIndebtedness,togetherwiththeprincipalamountofanyothersuchIndebtednessunderwhichtherehasbeenapaymentdefaultorthematurityofwhichhasbeensoaccelerated,aggregates$100.0millionormore(oritsforeigncurrencyequivalent);

(6) certaineventsofbankruptcy,insolvencyorreorganizationoftheCompanyoraSignificantSubsidiaryorgroupofSubsidiariesthat,takentogether(asofthedateofthelatestauditedconsolidatedfinancialstatementsfortheCompanyanditsSubsidiaries),wouldconstituteaSignificantSubsidiary(the"bankruptcyprovisions");

(7) failurebytheCompanyoranySignificantSubsidiaryorgroupofSubsidiariesthat,takentogether(asofthedateofthelatestauditedconsolidatedfinancialstatementsfortheCompanyanditsSubsidiaries),wouldconstituteaSignificantSubsidiarytopayfinalandnon-appealablejudgmentsaggregatinginexcessof$100.0million(oritsforeigncurrencyequivalent)(netofanyamountsthatarecoveredbyinsurance),whichjudgmentsremainunsatisfiedorundischargedforanyperiodof60consecutivedaysduringwhichastayofenforcementofsuchjudgmentsshallnotbeineffect(the"judgmentdefaultprovision").

However,adefaultunderclause(4)ofthisparagraphwillnotconstituteanEventofDefaultuntiltheTrusteeortheHoldersofatleast25%inprincipalamountofthethenoutstandingNotesnotifytheCompany(withcopytotheTrustee)ofthedefaultandtheCompanydoesnotcuresuchdefaultwithinthetimespecifiedinclause(4)ofthisparagraphafterreceiptofsuchnotice.

IfanEventofDefault(otherthananEventofDefaultdescribedinclause(6)abovewithrespecttotheCompany)occursandiscontinuing,theTrusteebynoticeinwritingspecifyingtheEventofDefaulttotheCompany,ortheHoldersofatleast25%inprincipalamountofthethenoutstandingNotesbynoticetotheCompanyandtheTrustee,maydeclaretheprincipalof,premium,ifany,andaccruedandunpaidinterest,ifany,onalltheNotestobedueandpayable.Uponsuchadeclaration,suchprincipal,premium,ifany,andaccruedandunpaidinterest,ifany,willbedueandpayableimmediately.IntheeventofadeclarationofaccelerationoftheNotesbecauseanEventofDefaultdescribedinclause(5)abovehasoccurredandiscontinuing,thedeclarationofaccelerationoftheNotesshallbeautomaticallyrescindedandannulledifthedefaulttriggeringsuchEventofDefaultpursuanttoclause(5)shallberemediedorcuredbytheCompanyoraSubsidiaryorwaivedbytherequisiteholdersoftherelevantIndebtednesswithin30daysafterthedeclarationofaccelerationwithrespecttheretoandif(1)theannulmentoftheaccelerationoftheNoteswouldnotconflictwithanyjudgmentordecreeofacourtofcompetentjurisdictionand(2)allexistingEventsofDefault,except

S-41

Page 51: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

nonpaymentofprincipal,premiumorinterestontheNotesthatbecameduesolelybecauseoftheaccelerationoftheNotes,havebeencuredorwaived.

IfanEventofDefaultdescribedinclause(6)aboveoccursandiscontinuingwithrespecttotheCompany,theprincipalof,premium,ifany,andaccruedandunpaidinterest,ifany,onalltheNoteswillbecomeandbeimmediatelydueandpayablewithoutanydeclarationorotheractonthepartoftheTrusteeoranyHolders.TheHoldersofamajorityinprincipalamountoftheoutstandingNotesmaywaiveallpastdefaults(exceptwithrespecttononpaymentofprincipal,premiumorinterest)andrescindanysuchaccelerationwithrespecttotheNotesanditsconsequencesif(1)rescissionwouldnotconflictwithanyjudgmentordecreeofacourtofcompetentjurisdictionand(2)allexistingEventsofDefault,otherthanthenonpaymentoftheprincipalof,premium,ifany,andinterestontheNotesthathavebecomeduesolelybysuchdeclarationofacceleration,havebeencuredorwaived.

IfanEventofDefaultoccursandiscontinuing,theTrusteewillbeundernoobligationtoexerciseanyoftherightsorpowersundertheIndentureortheNotesattherequestordirectionofanyoftheHoldersunlesssuchHoldershaveofferedtotheTrusteeindemnityorsecuritysatisfactorytoitagainstanyloss,liabilityorexpense.Excepttoenforcetherighttoreceivepaymentofprincipal,premium,ifany,orinterestwhendue,noHoldermaypursueanyremedywithrespecttotheIndentureortheNotesunless:

(1) suchHolderhaspreviouslygiventheTrusteenoticethatanEventofDefaultiscontinuing;

(2) theHoldersofatleast25%inprincipalamountofthethenoutstandingNoteshaverequestedtheTrusteetopursuetheremedy;

(3) suchHoldershaveofferedtheTrusteesecurityorindemnitysatisfactorytotheTrusteeagainstanyloss,liabilityorexpense;

(4) theTrusteehasnotcompliedwithsuchrequestwithin60daysafterthereceiptoftherequestandtheofferofsecurityorindemnity;and

(5) theHoldersofamajorityinprincipalamountofthethenoutstandingNoteshavenotgiventheTrusteeadirectionthatisinconsistentwithsuchrequestwithinsuch60-dayperiod.

Subjecttocertainrestrictions,theHoldersofamajorityinprincipalamountofthethenoutstandingNotesaregiventherighttodirectthetime,methodandplaceofconductinganyproceedingforanyremedyavailabletotheTrusteeorofexercisinganytrustorpowerconferredontheTrustee.TheIndentureprovidesthatintheeventanEventofDefaulthasoccurredandiscontinuing,theTrusteewillberequiredintheexerciseofitspowerstousethedegreeofcarethataprudentpersonwoulduseunderthecircumstancesintheconductofhisorherownaffairs.TheTrustee,however,mayrefusetofollowanydirectionthatconflictswithlawortheIndentureortheNotesorthattheTrusteedeterminesingoodfaithisundulyprejudicialtotherightsofanyotherHolder(itbeingunderstoodthattheTrusteedoesnothaveanaffirmativedutytoascertainwhetherornotsuchdirectionsareundulyprejudicialtosuchHolders)orthatwouldinvolvetheTrusteeinpersonalliability.PriortotakinganyactionundertheIndenture,theTrusteewillbeentitledtosecurityorindemnificationsatisfactorytoitinitssolediscretionagainstalllosses,liabilitiesandexpensescausedbytakingornottakingsuchaction.

TheIndentureprovidesthatifaDefaultoccursandiscontinuingandisactuallyknowntoaresponsibleofficeroftheTrustee,theTrusteewillsendtoeachHoldernoticeoftheDefaultwithin90daysaftertheTrusteeobtainssuchknowledge.ExceptinthecaseofaDefaultinthepaymentofprincipalof,premium,ifany,orinterestonanyNote,theTrusteemaywithholdfromtheHoldersnoticeofanycontinuingDefaultiftheTrusteedeterminesingoodfaiththatwithholdingthenoticeisintheinterestsoftheHolders.Inaddition,theCompanyisrequiredtodelivertotheTrustee,within120daysaftertheendofeachfiscalyear(commencingwiththefiscalyearendingDecember31,2019),

S-42

Page 52: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

acertificateindicatingwhetherthesignersthereofknowofanyDefaultthatoccurredduringthepreviousyear.TheCompanyalsoisrequiredtodelivertotheTrustee,within30daysaftertheknowledgethereofifsucheventisstillcontinuing,writtennoticeofanyeventswhichwouldconstitutecertainDefaults,theirstatusandwhatactiontheCompanyistakingorproposingtotakeinrespectthereof.

Amendment, Supplement and Waiver

WithouttheconsentofanyHolders,theCompanyortheTrustee,atanytimeandfromtimetotime,mayenterintooneormoreindenturessupplementaltotheIndenturewithrespecttotheNotesforanyofthefollowingpurposes:

(1) toevidencethesuccessionofanotherPersontotheCompanyandtheassumptionbyanysuchsuccessorofthecovenantsoftheCompany,asapplicable,intheIndentureandtheNotes;

(2) toaddtothecovenantsoftheCompanyforthebenefitoftheHolders,ortosurrenderanyrightorpowerhereinconferredupontheCompany;

(3) toaddadditionalEventsofDefault;

(4) toprovideforuncertificatedNotesinadditiontoorinplaceofthecertificatedNotes;provided,thatsuchuncertificatedNotesareissuedinregisteredformforpurposesofSection163(f)oftheInternalRevenueCodeof1986,asamended;

(5) toevidenceandprovidefortheacceptanceofappointmentundertheIndenturebyasuccessorTrustee;

(6) toprovidefororconfirmtheissuanceofadditionaldebtsecuritiesinaccordancewiththetermsoftheIndenture;

(7) tocureanyambiguity,defect,omission,mistakeorinconsistency;

(8) tomakeanyotherprovisionswithrespecttomattersorquestionsarisingundertheIndenture;provided,however,thatsuchactionspursuanttothisclause(8)shallnotadverselyaffecttheinterestsoftheHoldersoftheNotesinanymaterialrespect,asdeterminedingoodfaithbytheBoardofDirectorsoftheCompany;

(9) toconformthetextoftheIndentureortheNotestoanyprovisionofthis"DescriptionofNotes";or

(10) toeffectormaintainthequalificationoftheIndentureundertheTrustIndentureAct.

WiththeconsentoftheHoldersofnotlessthanamajorityinaggregateprincipalamountoftheoutstandingNotes,theCompanyandtheTrusteemayenterintoanindentureorindenturessupplementaltotheIndentureforthepurposeofaddinganyprovisionstoorchanginginanymanneroreliminatinganyoftheprovisionsoftheIndentureapplicabletotheNotesorofsuchNotesorofmodifyinginanymannertherightsoftheHoldersoftheNotesundertheIndenture,includingthedefinitionstherein;provided,however,thatnosuchsupplementalindentureshall,withouttheconsentoftheHolderofeachoutstandingNoteaffectedthereby:

(1) changethefixedmaturityofanyNoteorofanyinstallmentofinterestonanyNote,orreducetheamountpayableinrespectoftheprincipalthereofortherateofinterestthereonoranypremiumpayablethereon,orreducetheamountthatwouldbedueandpayableonaccelerationofthematuritythereof,orchangetheplaceofpaymentwhere,orthecoinorcurrencyinwhich,anyNoteoranypremiumorinterestthereonispayable,orimpairtherighttoinstitutesuitfortheenforcementofanysuchpaymentonorafterthefixedmaturitythereof,orchangethedateonwhichanyNotesmaybesubjecttoredemption(exceptthose

S-43

Page 53: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

provisionsrelatingtothecovenantsdescribedaboveunderthecaption"RepurchaseattheOptionofHolders—ChangeofControlRepurchaseEvent")orreducetheredemptionpricetherefor,

(2) reducethepercentageinaggregateprincipalamountoftheoutstandingNotes,theconsentofwhoseHoldersisrequiredforanysuchsupplementalindenture,ortheconsentofwhoseHoldersisrequiredforanywaiver(ofcompliancewithcertainprovisionsoftheIndentureorcertaindefaultsthereunderandtheirconsequences)providedforintheIndenture,

(3) modifyorchangeanyprovisionoftheIndentureaffectingtherankingoftheNotesinamanneradversetotheHoldersoftheNotes,or

(4) modifyanyoftheprovisionsofthisparagraphorprovisionsrelatingtowaiverofdefaultsorcertaincovenants,excepttoincreaseanysuchpercentagerequiredforsuchactionsortoprovidethatcertainotherprovisionsoftheIndenturecannotbemodifiedorwaivedwithouttheconsentoftheHolderofeachoutstandingNoteaffectedthereby.

TheHoldersofnotlessthanamajorityinaggregateprincipalamountoftheoutstandingNotesmayonbehalfoftheHoldersofalltheNoteswaiveanypastdefaultundertheIndentureanditsconsequences,exceptadefault:

(1) inanypaymentinrespectoftheprincipalof(orpremium,ifany)orinterestonanyNotes,or

(2) inrespectofacovenantorprovisionhereofwhichundertheIndenturecannotbemodifiedoramendedwithouttheconsentoftheHolderofeachoutstandingNoteaffected.

Satisfaction and Discharge of the Indenture; Defeasance

TheCompanymayterminateitsobligationsundertheIndenturewithrespecttotheNoteswhen:

(1) either:(A)allNotestheretoforeauthenticatedanddeliveredhavebeendeliveredtotheTrusteeforcancellationor(B)allsuchNotesnottheretoforedeliveredtotheTrusteeforcancellation(i)havebecomedueandpayableor(ii)willbecomedueandpayablewithinoneyearoraretobecalledforredemptionwithinoneyear(a"Discharge")underirrevocablearrangementsforthegivingofnoticeofredemptionbytheTrusteeinthename,andattheexpense,oftheCompany,andtheCompanyhasirrevocablydepositedorcausedtobedepositedwiththeTrusteefundsinanamountsufficienttopayanddischargetheentireindebtednessontheNotes,nottheretoforedeliveredtotheTrusteeforcancellation,forprincipalof,premium,ifany,andinteresttotheStatedMaturityordateofredemption;

(2) theCompanyhaspaidorcausedtobepaidallothersumsthendueandpayableundertheIndenturebytheCompanywithrespecttotheNotes;

(3) thedepositwillnotresultinabreachorviolationof,orconstituteadefaultunder,anyothermaterialinstrumenttowhichtheCompanyisapartyorbywhichtheCompanyisbound;

(4) theCompanyhasdeliveredirrevocableinstructionstotheTrusteeundertheIndenturetoapplythedepositedmoneytowardthepaymentoftheNotesatmaturityorontheredemptiondate,asthecasemaybe;and

(5) theCompanyhasdeliveredtotheTrusteeanOfficer'sCertificateandanopinionofcounselreasonablyacceptabletotheTrustee,eachstatingthatallconditionsprecedentundertheIndenturerelatingtotheDischargeoftheNoteshavebeencompliedwith.

S-44

Page 54: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

TheCompanymayelect,atitsoption,tohaveitsobligationswithrespecttotheoutstandingNotesdischarged("defeasance").SuchdefeasancemeansthattheCompanywillbedeemedtohavepaidanddischargedtheentireindebtednessrepresentedbytheoutstandingNotes,exceptfor:

(1) therightsofHoldersofsuchNotestoreceivepaymentsinrespectoftheprincipalofandanypremiumandinterestonsuchNoteswhenpaymentsaredue,

(2) theCompany'sobligationswithrespecttosuchNotesconcerningissuingtemporaryNotes,registrationofNotes,mutilated,destroyed,lostorstolenNotesandthemaintenanceofanofficeoragencyforpaymentandmoneyforsecuritypaymentsheldintrust,

(3) therights,powers,trusts,dutiesandimmunitiesoftheTrusteeandtheCompany'sobligationsinconnectionwiththeIndenture,

(4) theCompany'srightofoptionalredemption,and

(5) thedefeasanceprovisionsoftheIndenture.

Inaddition,theCompanymayelect,atitsoption,tohavetheobligationsoftheCompanyreleasedwithrespecttocertaincovenantsintheIndenture("covenantdefeasance")andanyomissiontocomplywithsuchobligationshallnotconstituteaDefaultwithrespecttotheNotes.Intheeventcovenantdefeasanceoccurs,certainevents(notincludingnon-paymentandbankruptcyandinsolvencyeventswithrespecttotheCompany)describedunder"EventsofDefault"willnolongerconstituteanEventofDefaultwithrespecttotheNotes.

InordertoexerciseeitherdefeasanceorcovenantdefeasancewithrespecttotheoutstandingNotes:

(1) theCompanymustirrevocablyhavedepositedorcausedtobedepositedwiththeTrusteeastrustfundsintrustforthepurposeofmakingthefollowingpayments,specificallypledgedassecurityfor,anddedicatedsolelytothebenefitsoftheHoldersofsuchNotes:(A)moneyinanamountor(B)U.S.governmentobligations,whichthroughthescheduledpaymentofprincipalandinterestinrespectthereofinaccordancewiththeirtermswillprovide,notlaterthantheduedateofanypayment,moneyinanamountor(C)acombinationthereof,ineachcasesufficientwithoutreinvestment,intheopinionofanationallyrecognizedfirmofindependentpublicaccountantsexpressedinawrittencertificationthereofdeliveredtotheTrustee,topayanddischarge,andwhichshallbeappliedbytheTrusteetopayanddischarge,theentireindebtednessinrespectoftheprincipalofandpremium,ifany,andinterestonsuchNotesontheStatedMaturitythereofor(iftheCompanyhasmadeirrevocablearrangementssatisfactorytotheTrusteeforthegivingofnoticeofredemptionbytheTrusteeinthenameandattheexpenseoftheCompany)theredemptiondatethereof,asthecasemaybe,inaccordancewiththetermsoftheIndentureandsuchNotes;

(2) inthecaseofdefeasance,theCompanyshallhavedeliveredtotheTrusteeanopinionofcounselstatingthat(A)theCompanyhasreceivedfrom,ortherehasbeenpublishedby,theInternalRevenueServicearulingor(B)sincetheIssueDate,therehasbeenachangeintheapplicableUnitedStatesfederalincometaxlaw,ineithercase(A)or(B)totheeffectthat,andbasedthereonsuchopinionshallconfirmthat,theHoldersandbeneficialownersofsuchoutstandingNoteswillnotrecognizegainorlossforUnitedStatesfederalincometaxpurposesasaresultofthedeposit,defeasanceanddischargetobeeffectedwithrespecttosuchNotesandwillbesubjecttoUnitedStatesfederalincometaxonthesameamount,inthesamemannerandatthesametimesaswouldbethecaseifsuchdeposit,defeasanceanddischargewerenottooccur;

(3) inthecaseofcovenantdefeasance,theCompanyshallhavedeliveredtotheTrusteeanopinionofcounseltotheeffectthattheHoldersandbeneficialownersofsuchoutstanding

S-45

Page 55: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

NoteswillnotrecognizegainorlossforUnitedStatesfederalincometaxpurposesasaresultofthedepositandcovenantdefeasancetobeeffectedwithrespecttosuchNotesandwillbesubjecttoUnitedStatesfederalincometaxonthesameamount,inthesamemannerandatthesametimesaswouldbethecaseifsuchdepositandcovenantdefeasancewerenottooccur;

(4) noDefaultwithrespecttotheoutstandingNotesshallhaveoccurredandbecontinuingatthetimeofsuchdepositaftergivingeffectthereto(otherthanaDefaultresultingfromtheborrowingoffundstobeappliedtosuchdepositandthegrantofanyLientosecuresuchborrowing);

(5) suchdefeasanceorcovenantdefeasanceshallnotresultinabreachorviolationof,orconstituteadefaultunder,anymaterialagreementormaterialinstrument(otherthantheIndenture)towhichtheCompanyoranyofitsSubsidiariesisapartyorbywhichtheCompanyoranyofitsSubsidiariesisapartyisbound;and

(6) theCompanyshallhavedeliveredtotheTrusteeanOfficer'sCertificateandanopinionofcounsel,eachstatingthatallconditionsprecedentwithrespecttosuchdefeasanceorcovenantdefeasancehavebeencompliedwith.

Notwithstandingtheforegoing,theopinionofcounselrequiredbyclause(2)or(3)abovewithrespecttoadefeasanceorcovenantdefeasanceneednottobedeliveredifallNotesnotthereforedeliveredtotheTrusteeforcancellation(x)havebecomedueandpayableor(y)willbecomedueandpayableatStatedMaturitywithinoneyearoraretobecalledforredemptionwithinoneyearunderirrevocablearrangementssatisfactorytotheTrusteeforthegivingofnoticeofredemptionbytheTrusteeinthename,andattheexpense,oftheCompany.

The Trustee

U.S.BankNationalAssociation,theTrusteeoftheNotesundertheIndenture,willbetheinitialpayingagentandregistrarfortheNotes.TheTrusteeoritsaffiliatesfromtimetotimemayextendcredittoandtransactotherbusinesswiththeCompanyinthenormalcourseofbusiness.ExceptduringthecontinuanceofanEventofDefault,theTrusteewillperformonlysuchdutiesasarespecificallysetforthintheIndenture.DuringthecontinuanceofanEventofDefaultthathasnotbeencuredorwaived,theTrusteewillexercisesuchoftherightsandpowersvestedinitbytheIndentureandusethesamedegreeofcareandskillintheirexercise,asaprudentpersonwouldexerciseoruseunderthecircumstancesintheconductofsuchperson'sownaffairs.

TheIndentureandtheTrustIndentureActcontaincertainlimitationsontherightsoftheTrustee,shoulditbecomeacreditoroftheCompany,toobtainpaymentofclaimsincertaincasesortorealizeoncertainpropertyreceivedinrespectofanysuchclaimassecurityorotherwise.TheTrusteewillbepermittedtoengageinothertransactions;however,ifitacquiresany"conflictinginterest"(asdefinedintheTrustIndentureAct)itmusteliminatesuchconflictwithin90days,applytotheCommissionforpermissiontocontinueorresign.

TheHoldersofamajorityinprincipalamountoftheoutstandingNoteswillhavetherighttodirectthetime,methodandplaceofconductinganyproceedingforanyremedyavailabletotheTrusteewithrespecttotheNotesorexercisinganytrustorpowerconferredontheTrusteewithrespecttosuchNotes,subjecttocertainexceptions.TheIndentureprovidesthatincaseanEventofDefaulthasoccurredandiscontinuing,theTrusteeshallexercisesuchoftherightsandpowersvestedinitbytheIndenture,andusethesamedegreeofcareandskillintheirexercise,asaprudentpersonwouldexerciseoruseunderthecircumstancesintheconductofsuchperson'sownaffairs.Subjecttosuchprovisions,theTrusteeshallbeundernoobligationtoexerciseanyoftherightsorpowersvestedinitbytheIndenturewithrespecttotheNotesattherequestordirectionofanyoftheholdersoftheNotespursuanttotheIndenture,unlesssuchholdersshallhaveprovidedtotheTrusteesecurityorindemnitysatisfactorytotheTrusteeagainstthelosses,liabilitiesandexpenseswhichmightbeincurredbyitincompliancewithsuchrequestordirection.

S-46

Page 56: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Norecoursemay,tothefullextentpermittedbyapplicablelaw,betaken,directlyorindirectly,withrespecttotheobligationsoftheCompanyorundertheIndentureoranyrelateddocuments,anycertificateorotherwritingdeliveredinconnectiontherewith,against(i)theTrusteeinitsindividualcapacity,(ii)anypartner,owner,beneficiary,agent,officer,director,employee,agent,successororassignoftheTrustee,eachinitsindividualcapacityor(iii)anyholderofequityintheTrustee.

No Personal Liability of Stockholders, Partners, Officers or Directors

Nodirector,officer,employee,stockholder,generalorlimitedpartnerorincorporator,past,presentorfuture,oftheCompanyoranyofitsSubsidiaries,assuchorinsuchcapacity,shallhaveanypersonalliabilityforanyobligationsoftheCompanyundertheNotesortheIndenturebyreasonofhis,heroritsstatusassuchdirector,officer,employee,stockholder,generalorlimitedpartnerorincorporator.EachHolderofNotesbyacceptingaNotewaivesandreleasesallsuchliability.ThewaiverandreleasearepartoftheconsiderationfortheissuanceoftheNotes.

Governing Law

TheIndentureandtheNoteswillbegovernedby,andconstruedinaccordancewith,thelawsoftheStateofNewYork.

Certain Definitions

SetforthbelowisasummaryofcertainofthedefinedtermsusedintheIndenture.ReferenceismadetotheIndentureforthefulldefinitionofallsuchterms,aswellasanycapitalizedtermusedhereinforwhichnodefinitionisprovided.

"BoardofDirectors"means(i)withrespecttotheCompanyoranySubsidiary,itsboardofdirectorsoranydulyauthorizedcommitteethereoforspecifiedofficersandemployeesoftheCompanytowhichthepowersofsuchboardhavebeenlawfullydelegated;(ii)withrespecttoacorporation,theboardofdirectorsofsuchcorporationoranydulyauthorizedcommitteethereof;and(iii)withrespecttoanyotherentity,theboardofdirectorsorsimilarbodyofthegeneralpartnerormanagersofsuchentityoranydulyauthorizedcommitteethereof.

"CapitalLeaseObligation"means,atthetimeanydeterminationistobemade,theamountoftheliabilityinrespectofacapitalleasethatwouldatthattimeberequiredtobecapitalizedandreflectedasaliabilityonabalancesheet(excludingthefootnotesthereto)preparedinaccordancewithGAAP,andtheStatedMaturitythereofshallbethedateofthelastpaymentofrentoranyotheramountdueundersuchleasepriortothefirstdateuponwhichsuchleasemaybeprepaidbythelesseewithoutpaymentofapenalty.

"CapitalStock"meansanyandallshares,interests,participationsorotherequivalents(howeverdesignated)ofcapitalstockofacorporation,anyandallequivalentownershipinterestsinaPerson(otherthanacorporation)andanyandallwarrantsoroptionstopurchaseanyoftheforegoing.

"CashEquivalents"means(a)marketabledirectobligationsissuedby,orunconditionallyguaranteedby,theUnitedStatesgovernmentorissuedbyanyagencythereofandbackedbythefullfaithandcreditoftheUnitedStates,ineachcasematuringwithinoneyearfromthedateofacquisition;(b)certificatesofdeposit,timedeposits,eurodollartimedepositsorovernightbankdepositshavingmaturitiesoftwelvemonthsorlessfromthedateofacquisitionissuedbyanycommercialbankorganizedunderthelawsoftheUnitedStatesoranystatethereofhavingcombinedcapitalandsurplusofnotlessthan$500,000,000andashorttermdepositratingofatleastA-1byS&PandP-1byMoody's,orcarryinganequivalentratingbyanationallyrecognizedratingagency,ifbothofthetwonamedratingagenciesceasepublishingratingsofcommercialpaperissuersgenerally;(c)commercialpaperofanissuerratedatleastA-2byS&PandP-2byMoody'satthetimeof

S-47

Page 57: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

acquisitionthereof,orcarryinganequivalentratingbyanationallyrecognizedratingagency,ifbothofthetwonamedratingagenciesceasepublishingratingsofcommercialpaperissuersgenerally,andmaturingwithinninemonthsfromthedateofacquisition;(d)repurchaseobligationsofanyLenderorofanycommercialbanksatisfyingtherequirementsofclause(b)ofthisdefinition,havingatermofnotmorethan30days,withrespecttosecuritiesissuedorfullyguaranteedorinsuredbytheUnitedStatesgovernment;(e)securitieswithmaturitiesofoneyearorlessfromthedateofacquisitionissuedorfullyguaranteedbyanystate,commonwealthorterritoryoftheUnitedStates,byanypoliticalsubdivisionortaxingauthorityofanysuchstate,commonwealthorterritoryorbyanyforeigngovernment,thesecuritiesofwhichstate,commonwealth,territory,politicalsubdivision,taxingauthorityorforeigngovernment(asthecasemaybe)areratedatleastAbyS&PandA2byMoody's;(f)securitieswithmaturitiesofoneyearorlessfromthedateofacquisitionbackedbystandbylettersofcreditissuedbyanyLenderoranycommercialbanksatisfyingtherequirementsofclause(b)ofthisdefinition;or(g)sharesofmoneymarketmutualorsimilarfundsthatinvestexclusivelyinassetssatisfyingtherequirementsofclauses(a)through(f)ofthisdefinition.

"Commission"meanstheSecuritiesandExchangeCommission.

"Company"meansCNOFinancialGroup,Inc.,andanysuccessorthereto.

"continuing"means,withrespecttoanyDefaultorEventofDefault,thatsuchDefaultorEventofDefaulthasnotbeencuredorwaived.

"Default"meansanyeventthatis,orafternoticeorpassageoftime,orboth,wouldbe,anEventofDefault.

"ExchangeAct"meanstheSecuritiesExchangeActof1934,asamended.

"GAAP"meansgenerallyacceptedaccountingprinciplesintheUnitedStatesofAmericaasineffectasoftheIssueDate,includingthosesetforthintheopinionsandpronouncementsoftheAccountingPrinciplesBoardoftheAmericanInstituteofCertifiedPublicAccountantsandstatementsandpronouncementsoftheFinancialAccountingStandardsBoardorinsuchotherstatementsbysuchotherentityasapprovedbyasignificantsegmentoftheaccountingprofession.AllratiosandcomputationsbasedonGAAPcontainedintheIndenturewillbecomputedinconformitywithGAAP,exceptthatintheeventtheCompanyisacquiredinatransactionthatisaccountedforusingpurchaseaccounting,theeffectsoftheapplicationofpurchaseaccountingshallbedisregardedinthecalculationofsuchratiosandothercomputationscontainedintheIndenture.

"Guarantee"meansaguaranteeotherthanbyendorsementofnegotiableinstrumentsforcollectionintheordinarycourseofbusiness,directorindirect,inanymannerincluding,withoutlimitation,bywayofapledgeofassetsorthroughlettersofcreditorreimbursementagreementsinrespectthereof,ofalloranypartofanyIndebtedness(whetherarisingbyvirtueofpartnershiparrangements,orbyagreementstokeep-well,topurchaseassets,goods,securitiesorservices,totakeorpayortomaintainfinancialstatementconditionsorotherwise).

"HedgingObligations"means,withrespecttoanyspecifiedPerson,theobligationsofsuchPersonunder:

(1) currencyexchange,interestrateorcommodityswapagreements(whetherfromfixedtofloatingorfromfloatingtofixed),currencyexchange,interestrateorcommoditycapagreementsandcurrencyexchange,interestrateorcommoditycollaragreements;

(2) otheragreementsorarrangementsdesignedtomanageinterestratesorinterestraterisk;and

(3) otheragreementsorarrangementsdesignedtomanage,hedgeorprotectsuchPersonagainstfluctuationsincurrencyexchange,interestratesorcommodityprices.

"Holder"meansaPersoninwhosenameaNoteisregisteredinthesecurityregister.

S-48

Page 58: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

"Indebtedness"means,withrespecttoanyspecifiedPerson,anyindebtedness(includingprincipalandpremium)ofsuchPerson(excludingaccruedexpensesandtradepayables),whetherornotcontingent:

(1) inrespectofborrowedmoney;

(2) evidencedbybonds,notes,debenturesorsimilarinstrumentsorlettersofcredit(orreimbursementagreementsinrespectthereof);

(3) inrespectofbanker'sacceptances;

(4) representingCapitalLeaseObligations;

(5) representingthedeferredandunpaidbalanceofthepurchasepriceofanypropertyorservicesduemorethansixmonthsaftersuchpropertyisacquiredorsuchservicesarecompleted;or

(6) representinganyinterestrateHedgingObligations,

ifandtotheextentanyoftheprecedingitems(otherthanlettersofcreditandHedgingObligations)wouldappearasaliabilityuponabalancesheetofthespecifiedPersonpreparedinaccordancewithGAAP.Inaddition,theterm"Indebtedness"includesallIndebtednessofotherssecuredbyaLienonanyassetownedbythespecifiedPerson(whetherornotsuchIndebtednessisassumedbythespecifiedPerson)and,totheextentnototherwiseincluded,theGuaranteebythespecifiedPersonofanyIndebtednessofanyotherPerson(otherthanbyendorsementofnegotiableinstrumentsforcollectionintheordinarycourseofbusiness).IndebtednessshallbecalculatedwithoutgivingeffecttotheeffectsofStatementofFinancialAccountingStandardsNo.133andrelatedinterpretationstotheextentsucheffectswouldotherwiseincreaseordecreaseanamountofIndebtednessforanypurposeundertheIndentureasaresultofaccountingforanyembeddedderivativescreatedbythetermsofsuchIndebtedness;provided,however,thatnotwithstandingtheforegoing,Indebtednessshallbedeemednottoincludecontingentobligationsincurredinthenormalcourseofbusinessandnotinrespectofborrowedmoney.

"InsuranceSubsidiary"meansanySubsidiaryoftheCompanythatisrequiredtobelicensedasaninsurerorreinsurer.

"IssueDate"means,2019.

"Officer"meanstheChairmanoftheBoardofDirectors,theChiefExecutiveOfficer,thePresident,anyExecutiveVicePresident,anySeniorVicePresident,anyotherVicePresident,theSecretaryortheTreasureroftheCompany.

"Officer'sCertificate"meansacertificatesignedbyanOfficeroftheCompany.

"Person"meansanyindividual,corporation,limitedliabilitycompany,partnership,jointventure,trust,unincorporatedorganizationorgovernmentoranyagencyorpoliticalsubdivisionthereof.

"RelatedBusiness"meansanybusinessthatisthesameasorrelated,ancillaryorcomplementarytoanyofthebusinessesoftheCompanyanditsSubsidiariesontheIssueDateandanyreasonableextensionorevolutionofanyoftheforegoing.

"SignificantSubsidiary"meansanySubsidiarythatwouldbea"significantsubsidiary"asdefinedinArticle1,Rule1-02ofRegulationS-X,promulgatedpursuanttotheSecuritiesAct,assuchRegulationisineffectontheIssueDate.

"StatedMaturity,"whenusedwithrespecttoanyNoteoranyinstallmentofinterestthereon,meansthedatespecifiedinsuchNoteasthefixeddateonwhichtheprincipalamountofsuchNoteorsuchinstallmentofinterestisdueandpayableand,whenusedwithrespecttoanyinstallmentofinterestorprincipalonanyseriesofIndebtedness,thedateonwhichthepaymentofinterestor

S-49

Page 59: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

principalwasscheduledtobepaidinthedocumentationgoverningsuchIndebtednessasoftheIssueDate,andwillnotincludeanycontingentobligationstorepay,redeemorrepurchaseanysuchinterestorprincipalpriortothedateoriginallyscheduledforthepaymentthereof.

"Subsidiary"meansanycorporation,associationorotherbusinessentityofwhichmorethan50%,bynumberofvotes,oftheVotingStockisatthetimedirectlyorindirectlyownedbyusprovidedthat(i)WendoverLimited,(ii)RiskGridTechnologiesInc.,(iii)AITBioscienceLLC,(iv)CreekSourceLLCand(v)fortheavoidanceofdoubt,MillCreekCLOIILtd.,SilverCreekCLOLtd.,ClearCreekCLOLtd.,BeanCreekCLOLtd.,DeerCreekCLOLtd.andanyothervariableinterestentityformedaftertheIssueDateshallnotbeconsideredaSubsidiaryforanypurposeoftheIndenture.

"VotingStock"ofapersonmeansallclassesofCapitalStockofsuchpersonthenoutstandingandnormallyentitled(withoutregardtotheoccurrenceofanycontingency)tovoteintheelectionofdirectors(orpersonsperformingsimilarfunctions).

S-50

Page 60: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

CERTAIN UNITED STATES FEDERAL INCOME AND ESTATE TAX CONSEQUENCES TO NON-U.S. HOLDERS

ThefollowingisasummaryofcertainU.S.federalincomeandestatetaxconsequencesofthepurchase,ownershipanddispositionoftheNotesasofthedatehereof.Exceptwherenoted,thissummarydealsonlywithNotesthatareheldascapitalassetsforU.S.federalincometaxpurposesbyanon-U.S.holder(asdefinedbelow)whoacquirestheNotesuponoriginalissuanceattheirinitialissueprice.

A"non-U.S.holder"meansabeneficialowneroftheNotes(otherthananentitytreatedasapartnershipforU.S.federalincometaxpurposes)thatisnotforU.S.federalincometaxpurposesanyofthefollowing:

• acitizenorindividualresidentoftheUnitedStates;

• acorporation(oranyotherentitytreatedasacorporationforU.S.federalincometaxpurposes)createdororganizedinorunderthelawsoftheUnitedStates,anystatethereofortheDistrictofColumbia;

• anestatetheincomeofwhichissubjecttoU.S.federalincometaxationregardlessofitssource;or

• atrustifit(1)issubjecttotheprimarysupervisionofacourtwithintheUnitedStatesandoneormoreU.S.personshavetheauthoritytocontrolallsubstantialdecisionsofthetrustor(2)hasavalidelectionineffectunderapplicableU.S.TreasuryregulationstobetreatedasaU.S.person.

ThissummaryisbaseduponprovisionsoftheInternalRevenueCodeof1986,asamended(the"Code"),andregulations,rulingsandjudicialdecisionsasofthedatehereof.Thoseauthoritiesmaybechanged,perhapsretroactively,soastoresultinU.S.federalincomeandestatetaxconsequencesdifferentfromthosesummarizedbelow.ThissummarydoesnotaddressallaspectsofU.S.federalincomeandestatetaxes(includingtheMedicarecontributiontax)anddoesnotdealwithforeign,state,localorothertaxconsiderationsthatmayberelevanttonon-U.S.holdersinlightoftheirpersonalcircumstances.Inaddition,itdoesnotrepresentadetaileddescriptionoftheU.S.federalincomeandestatetaxconsequencesapplicabletoyouifyouaresubjecttospecialtreatmentundertheU.S.federalincometaxlaws(includingifyouareaU.S.expatriate,a"controlledforeigncorporation,"a"passiveforeigninvestmentcompany"orapartnershiporotherpass-throughentityforU.S.federalincometaxpurposes),and,inparticular,doesnotaddresstaxconsiderationsthatmaybeapplicabletoholdersofExisting2020Notesthatareredeemedinasubstantiallycontemporaneoustransaction.Wecannotassureyouthatachangeinlawwillnotaltersignificantlythetaxconsiderationsthatwedescribeinthissummary.

Ifapartnership(orotherentitytreatedasapartnershipforU.S.federalincometaxpurposes)holdstheNotes,thetaxtreatmentofapartnerwillgenerallydependuponthestatusofthepartnerandtheactivitiesofthepartnership.IfyouareapartnershiporapartnerofapartnershipholdingtheNotes,youshouldconsultyourtaxadvisors.

If you are considering the purchase of Notes, you should consult your own tax advisors concerning the particular U.S. federal income and estate taxconsequences to you of the purchase, ownership and disposition of the Notes, as well as the consequences to you arising under other U.S. federal tax lawsand the laws of any other taxing jurisdiction.

S-51

Page 61: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

U.S. Federal Withholding Tax

SubjecttothediscussionsofbackupwithholdingandFATCAbelow,U.S.federalwithholdingtaxwillnotapplytoanypaymentofinterestontheNotesunderthe"portfoliointerestrule,"providedthat:

• interestpaidontheNotesisnoteffectivelyconnectedwithyourconductofatradeorbusinessintheUnitedStates;

• youdonot(actuallyorconstructively)own10%ormoreofthetotalcombinedvotingpowerofallclassesofourvotingstockwithinthemeaningoftheCodeandapplicableU.S.Treasuryregulations;

• youarenotacontrolledforeigncorporationthatisrelated(directlyorindirectly)tousthroughstockownership;

• youarenotabankwhosereceiptofinterestontheNotesisdescribedinSection881(c)(3)(A)oftheCode;and

• either(a)youprovideyournameandaddressonaproperlyexecutedInternalRevenueService("IRS")FormW-8BENorW-8BEN-E(orotherapplicableform)andcertify,underpenaltiesofperjury,thatyouarenotaUnitedStatespersonasdefinedundertheCodeor(b)youholdyourNotesthroughcertainintermediariesandsatisfythecertificationrequirementsofapplicableU.S.Treasuryregulations.Specialcertificationrulesapplytonon-U.S.holdersthatarepass-throughentitiesratherthancorporationsorindividuals.

Ifyoucannotsatisfytherequirementsdescribedabove,paymentsofinterestmadetoyouwillbesubjecttoa30%U.S.federalwithholdingtax,unlessyouprovidetheapplicablewithholdingagentwithaproperlyexecuted:

• IRSFormW-8BENorW-8BEN-E(orotherapplicableform)claiminganexemptionfromorreductioninwithholdingunderthebenefitofanapplicableincometaxtreaty;or

• IRSFormW-8ECI(orotherapplicableform)statingthatinterestpaidontheNotesisnotsubjecttowithholdingtaxbecauseitiseffectivelyconnectedwithyourconductofatradeorbusinessintheUnitedStates(asdiscussedbelowunder"U.S.FederalIncomeTax").

The30%U.S.federalwithholdingtaxgenerallywillnotapplytoanypaymentofprincipalorgainthatyourealizeonthesale,exchange,retirementorotherdispositionofaNote.

U.S. Federal Income Tax

IfyouareengagedinatradeorbusinessintheUnitedStatesandinterestontheNotesiseffectivelyconnectedwiththeconductofthattradeorbusiness(and,ifrequiredbyanapplicableincometaxtreaty,isattributabletoaU.S.permanentestablishment),thenyouwillbesubjecttoU.S.federalincometaxonthatinterestonanetincomebasis(althoughyouwillbeexemptfromthe30%U.S.federalwithholdingtax,providedthecertificationrequirementsdiscussedabovein"U.S.FederalWithholdingTax"aresatisfied)inthesamemannerasifyouwereaUnitedStatespersonasdefinedundertheCode.Inaddition,ifyouareaforeigncorporation,youmaybesubjecttoabranchprofitstaxequalto30%(orlowerapplicableincometaxtreatyrate)ofyoureffectivelyconnectedearningsandprofits,subjecttoadjustments.

SubjecttothediscussionsofbackupwithholdingandFATCAbelow,anygainrealizedonthedispositionofaNotegenerallywillnotbesubjecttoU.S.federalincometaxunless:

• thegainiseffectivelyconnectedwithyourconductofatradeorbusinessintheUnitedStates(and,ifrequiredbyanapplicableincometaxtreaty,isattributabletoaU.S.permanent

S-52

Page 62: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

establishment),inwhichcasesuchgainwillgenerallybesubjecttoU.S.federalincometax(andpossiblybranchprofitstax)inthesamemanneraseffectivelyconnectedinterestasdescribedabove;or

• youareanindividualwhoispresentintheUnitedStatesfor183daysormoreinthetaxableyearofthatdisposition,andcertainotherconditionsaremet,inwhichcase,unlessanapplicableincometaxtreatyprovidesotherwise,youwillgenerallybesubjecttoa30%U.S.federalincometaxonanygainrecognized,whichmaybeoffsetbycertainU.S.sourcelosses.

U.S. Federal Estate Tax

IfyouareanindividualandarenotaU.S.citizenoraresidentoftheUnitedStates(asspecificallydefinedforU.S.federalestatetaxpurposes),yourestatewillnotbesubjecttoU.S.federalestatetaxontheNotesbeneficiallyownedbyyouatthetimeofyourdeath,providedthatanypaymenttoyouofinterestontheNotes,ifreceivedatsuchtime,wouldbeeligibleforexemptionfromthe30%U.S.federalwithholdingtaxunderthe"portfoliointerestrule"describedaboveunder"U.S.FederalWithholdingTax"withoutregardtothestatementrequirementdescribedinthefifthbulletpointofthatsection.

Information Reporting and Backup Withholding

Interestpaidtoyouandtheamountoftax,ifany,withheldwithrespecttothosepaymentsgenerallywillbereportedtotheIRS.Copiesoftheinformationreturnsreportingsuchinterestpaymentsandanywithholdingmayalsobemadeavailabletothetaxauthoritiesinthecountryinwhichyouresideundertheprovisionsofanapplicableincometaxtreaty.

Ingeneral,youwillnotbesubjecttobackupwithholdingwithrespecttopaymentsontheNotesthatwemaketoyouprovidedthattheapplicablewithholdingagentdoesnothaveactualknowledgeorreasontoknowthatyouareaUnitedStatespersonasdefinedundertheCode,andsuchwithholdingagenthasreceivedfromyouthestatementdescribedaboveinthefifthbulletpointunder"U.S.FederalWithholdingTax."

Informationreportingand,dependingonthecircumstances,backupwithholdingwillapplytotheproceedsofasaleorotherdisposition(includingaretirementorredemption)oftheNoteswithintheUnitedStatesorconductedthroughcertainU.S.-relatedfinancialintermediaries,unlessyoucertifyunderpenaltiesofperjurythatyouarenotaUnitedStatespersonasdefinedundertheCode(andthepayordoesnothaveactualknowledgeorreasontoknowthatyouareaUnitedStatespersonasdefinedundertheCode),oryouotherwiseestablishanexemption.

Backupwithholdingisnotanadditionaltax.AnyamountswithheldunderthebackupwithholdingruleswillbeallowedasarefundoracreditagainstyourU.S.federalincometaxliabilityprovidedtherequiredinformationistimelyfurnishedtotheIRS.

Additional Withholding Requirements

UnderSections1471through1474oftheCode(suchSectionscommonlyreferredtoas"FATCA"),a30%U.S.federalwithholdingtaxmayapplytoanyinterestontheNotesthatispaidto(i)a"foreignfinancialinstitution"(asspecificallydefinedintheCode)whichdoesnotprovidesufficientdocumentation,typicallyonIRSFormW-8BEN-E,evidencingeither(x)anexemptionfromFATCA,or(y)itscompliance(ordeemedcompliance)withFATCA(whichmayalternativelybeintheformofcompliancewithanintergovernmentalagreementwiththeUnitedStates)inamannerwhichavoidswithholding,or(ii)a"non-financialforeignentity"(asspecificallydefinedintheCode)whichdoesnotprovidesufficientdocumentation,typicallyonIRSFormW-8BEN-E,evidencingeither(x)anexemptionfromFATCA,or(y)adequateinformationregardingcertainsubstantialUnitedStates

S-53

Page 63: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

beneficialownersofsuchentity(ifany).IfaninterestpaymentisbothsubjecttowithholdingunderFATCAandsubjecttothewithholdingtaxdiscussedaboveunder"U.S.FederalWithholdingTax,"thewithholdingunderFATCAmaybecreditedagainst,andthereforereduce,suchotherwithholdingtax.

WhilewithholdingunderFATCAwouldalsohaveappliedtopaymentsofgrossproceedsfromthesaleorotherdispositionoftheNotesonorafterJanuary1,2019,recentlyproposedU.S.TreasuryregulationseliminateFATCAwithholdingonpaymentsofgrossproceedsentirely.AlthoughtheserecentlyproposedU.S.Treasuryregulationsarenotfinal,taxpayersgenerallymayrelyonthemuntilfinalU.S.Treasuryregulationsareissued.

YoushouldconsultyourowntaxadvisorsregardingtheserulesandwhethertheymayberelevanttoyourownershipanddispositionofNotes.

S-54

Page 64: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

CERTAIN ERISA CONSIDERATIONS

ThefollowingisasummaryofcertainconsiderationsassociatedwiththepurchaseandholdingoftheNotesby(i)employeebenefitplansthataresubjecttoTitleIoftheU.S.EmployeeRetirementIncomeSecurityActof1974,asamended("ERISA"),(ii)plans,individualretirementaccounts("IRAs")andotherarrangementsthataresubjecttoSection4975oftheU.S.InternalRevenueCodeof1986,asamended(the"Code"),(iii)provisionsunderanyotherU.S.ornon-U.S.federal,state,localorotherlawsorregulationsthataresimilartosuchprovisionsofERISAortheCode(collectively,"SimilarLaws"),and(iv)entitieswhoseunderlyingassetsareconsideredtoincludeplanassetswithinthemeaningof29C.F.R.Section2510.3-101(asmodifiedbySection3(42)ofERISA),orotherwise,ofanysuchplans,accountsandarrangementsdescribedinclauses(i),(ii)and(iii)(andeachsuchplan,accountandarrangementasdescribedinclauses(i)–(iv)referredtoasa"Plan").

General Fiduciary Matters

ERISAandtheCodeimposecertaindutiesonpersonswhoarefiduciariesofaPlansubjecttoTitleIofERISAorSection4975oftheCode(a"CoveredPlan")andprohibitcertaintransactionsinvolvingtheassetsofaCoveredPlananditsfiduciariesorotherinterestedparties.UnderERISAandtheCode,anypersonwhoexercisesanydiscretionaryauthorityorcontrolovertheadministrationofsuchaCoveredPlanorthemanagementordispositionoftheassetsofsuchaCoveredPlan,orwhorendersinvestmentadviceforafeeorothercompensationtosuchaCoveredPlan,isgenerallyconsideredtobeafiduciaryoftheCoveredPlan.

InconsideringaninvestmentintheNotesofaportionoftheassetsofanyPlan,afiduciaryshoulddeterminewhethertheinvestmentisinaccordancewiththedocumentsandinstrumentsgoverningthePlanandtheapplicableprovisionsofERISA,theCodeoranySimilarLawandtheavailability,ifnecessary,ofanyexemptivereliefunderanysuchlawsorregulations.Inaddition,afiduciaryofaPlanshouldconsultwithitscounselinordertodetermineiftheinvestmentsatisfiesthefiduciary'sdutiestothePlanincluding,withoutlimitation,theprudence,diversification,delegationofcontrolandprohibitedtransactionprovisionsofERISA,theCodeandanyotherapplicableSimilarLaws.

EachCoveredPlanshouldconsiderthefactthatnoneoftheCompany,theunderwritersoranyoftheirrespectiveaffiliates(the"TransactionParties")hasactedasaCoveredPlan'sfiduciary,orhasbeenrelieduponforanyadvice,withrespecttotheCoveredPlan'sdecisiontopurchaseorholdtheNotes.Allcommunications,correspondenceandmaterialsfromtheTransactionPartieswithrespecttotheNotesareintendedtobegeneralinnatureandarenotdirectedatanyspecificpurchaseroftheNotes,anddonotconstituteadviceregardingtheadvisabilityofinvestmentintheNotesforanyspecificpurchaser.ThedecisiontopurchaseandholdtheNotesmustbemadesolelybyeachprospectiveCoveredPlanpurchaseronanarm'slengthbasis.

Prohibited Transaction Issues

Section406ofERISAandSection4975oftheCodeprohibitCoveredPlansfromengaginginspecifiedtransactionsinvolvingplanassetswithpersonsorentitieswhoare"partiesininterest,"withinthemeaningofERISA,or"disqualifiedpersons,"withinthemeaningofSection4975oftheCode,unlessanexemptionisavailable.Apartyininterestordisqualifiedpersonwhoengagedinanon-exemptprohibitedtransactionmaybesubjecttoexcisetaxesandotherpenaltiesandliabilitiesunderERISAandtheCode.Inaddition,thefiduciaryoftheCoveredPlanthatengagedinsuchanon-exemptprohibitedtransactionmaybesubjecttopenaltiesandliabilitiesunderERISAandtheCode.Theacquisitionand/orholdingofNotesbyaCoveredPlanwithrespecttowhichaTransactionPartyisconsideredapartyininterestoradisqualifiedpersonmayconstituteorresultinadirectorindirectprohibitedtransactionunderSection406ofERISAand/orSection4975oftheCode,unlesstheinvestmentisacquiredandisheldinaccordancewithanapplicablestatutoryoradministrative

S-55

Page 65: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

exemption.Inthisregard,theU.S.DepartmentofLaborhasissuedprohibitedtransactionclassexemptions,or"PTCEs,"thatmayapplytothepurchaseandholdingoftheNotes.Theseclassexemptionsinclude,withoutlimitation,PTCE84-14respectingtransactionsdeterminedbyindependentqualifiedprofessionalassetmanagers,PTCE90-1respectinginsurancecompanypooledseparateaccounts,PTCE91-38respectingbankcollectiveinvestmentfunds,PTCE95-60respectinglifeinsurancecompanygeneralaccountsandPTCE96-23respectingtransactionsdeterminedbyin-houseassetmanagers.Inaddition,Section408(b)(17)ofERISAandSection4975(d)(20)oftheCodeproviderelieffromtheprohibitedtransactionprovisionsofERISAandSection4975oftheCodeforcertaintransactions,providedthatneithertheissuerofthesecuritiesnoranyofitsaffiliates(directlyorindirectly)haveorexerciseanydiscretionaryauthorityorcontrolorrenderanyinvestmentadvicewithrespecttotheassetsofanyCoveredPlaninvolvedinthetransactionandprovidedfurtherthattheCoveredPlanpaysnomorethanadequateconsiderationinconnectionwiththetransaction.Eachoftheabove-notedexemptionscontainsconditionsandlimitationsonitsapplication.FiduciariesofCoveredPlansconsideringacquiringand/orholdingtheNotesinrelianceontheseoranyotherexemptionshouldcarefullyreviewtheexemptioninconsultationwithcounseltoassureitisapplicable.Therecanbeno,andwedonotprovideany,assurancethatalloftheconditionsofanysuchexemptionswillbesatisfied.

Becauseoftheforegoing,theNotesshouldnotbepurchasedorheldbyanypersoninvesting"planassets"ofanyPlan,unlesssuchpurchaseandholdingwillnotconstituteanon-exemptprohibitedtransactionunderERISAandtheCodeorasimilarviolationofanyapplicableSimilarLaws.

Representation

ByacceptanceoftheNotes,eachpurchaserandsubsequenttransfereeoftheNoteswillbedeemedtohaverepresentedandwarrantedthateither(i)noportionoftheassetsusedbysuchpurchaserortransfereetopurchaseorholdtheNotesconstitutesassetsofanyPlanor(ii)(A)thepurchaseandholdingoftheNotesbysuchpurchaserortransfereewillnotconstituteanon-exemptprohibitedtransactionunderSection406ofERISAorSection4975oftheCodeorasimilarviolationunderanyapplicableSimilarLaws,and(B)noneoftheTransactionPartieshaveactedasafiduciarytoanyPlanwithrespecttothedecisiontopurchaseorholdtheNotesorbeenrelieduponforanyadvicewithrespecttothedecisiontopurchaseorholdtheNotes.

Theforegoingdiscussionisgeneralinnatureandisnotintendedtobeallinclusive.Duetothecomplexityoftheserulesandthepenaltiesthatmaybeimposeduponpersonsinvolvedinnon-exemptprohibitedtransactions,itisparticularlyimportantthatfiduciaries,orotherpersonsconsideringpurchasingorholdingtheNotesonbehalfof,orwiththeassetsof,anyPlan,consultwiththeircounselregardingthepotentialapplicabilityofERISA,Section4975oftheCodeandanySimilarLawstosuchinvestmentandwhetheranexemptionwouldbeapplicabletothepurchaseandholdingoftheNotes.PurchasersoftheNoteshaveexclusiveresponsibilityforensuringthattheirpurchaseandholdingoftheNotesdonotviolatethefiduciaryorprohibitedtransactionrulesofERISA,theCodeoranySimilarLaws.ThesaleofanyNotestoaPlanisinnorespectarepresentationbytheissueroranyofitsaffiliatesorrepresentativesthatsuchaninvestmentmeetsallrelevantlegalrequirementswithrespecttoinvestmentsbyanysuchPlangenerallyoranyparticularPlan,orthatsuchinvestmentisappropriateforsuchPlansgenerallyoranyparticularPlan.

NeitherthisdiscussionnoranythingprovidedinthisprospectussupplementisorisintendedtobeinvestmentadvicedirectedatanypotentialPlanpurchasersoratPlanpurchasersgenerallyandsuchpurchasersofanyNotes(orbeneficialintereststherein)shouldconsultandrelyontheirowncounselandadvisersastowhetheraninvestmentintheNotesissuitableforthePlan.

S-56

Page 66: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

UNDERWRITING

ThecompanyandtheunderwritersfortheofferingnamedbelowhaveenteredintoanunderwritingagreementwithrespecttotheNotes.Subjecttocertainconditions,eachunderwriternamedbelow,forwhomGoldmanSachs&Co.LLC,BarclaysCapitalInc.,KeyBancCapitalMarketsInc.andRBCCapitalMarkets,LLCareactingasrepresentatives,hasseverallyagreedtopurchasetheprincipalamountofNotesindicatedinthefollowingtable.

TheunderwritersarecommittedtotakeandpayforalloftheNotesbeingoffered,ifanyaretaken.

Notessoldbytheunderwriterstothepublicwillinitiallybeofferedatthepublicofferingpricesetforthonthecoverofthisprospectussupplement.AnyNotessoldbytheunderwriterstosecuritiesdealersmaybesoldatadiscountfromthepublicofferingpriceofuptooftheprincipalamountoftheNotes.AnysuchsecuritiesdealersmayresellanysuchNotespurchasedfromtheunderwriterstocertainotherbrokersordealersatadiscountfromthepublicofferingpriceofuptooftheprincipalamountoftheNotes.IfallsuchNotesarenotsoldattheofferingprice,theunderwritersmaychangetheofferingpriceandtheothersellingterms.TheofferingoftheNotesbytheunderwritersissubjecttoreceiptandacceptanceandsubjecttotheunderwriters'righttorejectanyorderinwholeorinpart.

TheNotesareanewissueofsecuritieswithnoestablishedtradingmarket.CNOhasbeenadvisedbytheunderwritersthatoneormoreoftheunderwritersintendtomakeamarketintheNotesbutarenotobligatedtodosoandmaydiscontinuemarketmakingatanytimewithoutnotice.NoassurancecanbegivenastotheliquidityofthetradingmarketfortheNotes.

WehaveagreedforaperiodfromthedateofthisprospectussupplementthroughandincludingtheissuedateoftheNotes,withoutthepriorwrittenconsentoftherepresentatives,nottooffer,sell,contracttosellorotherwisedisposeofanydebtsecuritiesthatareissuedorguaranteedbyusandthathaveatenorofmorethanoneyear.

ItisexpectedthatdeliveryoftheNoteswillbemadeagainstpaymentthereforonorabout,2019,whichwillbethebusinessdayfollowingthedateofpricingoftheNotes(suchsettlementperiodbeinghereinreferredtoasT+).PurchasersofNotesshouldbeawarethattheabilitytosettlesecondarymarkettradesoftheNoteseffectedonthedateofpricingmaybeaffectedbytheT+settlement.

Inconnectionwiththeoffering,theunderwritersmaypurchaseandsellNotesintheopenmarket.Thesetransactionsmayincludeshortsales,stabilizingtransactionsandpurchasestocoverpositionscreatedbyshortsales.ShortsalesinvolvethesalebytheunderwritersofagreaternumberofNotesthantheyarerequiredtopurchaseintheoffering.StabilizingtransactionsconsistofcertainbidsorpurchasesmadeforthepurposeofpreventingorretardingadeclineinthemarketpriceoftheNoteswhiletheofferingisinprogress.

S-57

Underwriters Principal Amount

of Notes GoldmanSachs&Co.LLC $ BarclaysCapitalInc. KeyBancCapitalMarketsInc. RBCCapitalMarkets,LLC BofASecurities,Inc. DeutscheBankSecuritiesInc. Total $ 425,000,000

Page 67: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Theunderwritersalsomayimposeapenaltybid.ThisoccurswhenaparticularunderwriterrepaystotheunderwritersaportionoftheunderwritingdiscountreceivedbyitbecausetherepresentativeshaverepurchasedNotessoldbyorfortheaccountofsuchunderwriterinstabilizingorshortcoveringtransactions.

Theseactivitiesbytheunderwriters,aswellasotherpurchasesbytheunderwritersfortheirownaccounts,maystabilize,maintainorotherwiseaffectthemarketpriceoftheNotes.Asaresult,thepriceoftheNotesmaybehigherthanthepricethatotherwisemightexistintheopenmarket.Iftheseactivitiesarecommenced,theymaybediscontinuedbytheunderwritersatanytime.Thesetransactionsmaybeeffectedintheover-the-countermarketorotherwise.

CNOestimatesthatitsshareofthetotalexpensesoftheoffering,excludingunderwritingdiscounts,willbeapproximately$million.Wehavealsoagreedtoreimbursetheunderwritersforcertainoftheirexpenses.

CNOhasagreedtoindemnifytheseveralunderwritersagainstcertainliabilities,includingliabilitiesundertheSecuritiesActof1933,ortocontributetopaymentswhichtheunderwritersmayberequiredtomakeinrespectofanysuchliabilities.

Theunderwritersandtheirrespectiveaffiliatesarefullservicefinancialinstitutionsengagedinvariousactivities,whichmayincludesalesandtrading,commercialandinvestmentbanking,advisory,investmentmanagement,investmentresearch,principalinvestment,hedging,marketmaking,brokerageandotherfinancialandnon-financialactivitiesandservices.Certainoftheunderwritersandtheirrespectiveaffiliateshaveprovided,andmayinthefutureprovide,avarietyoftheseservicestotheissuerandtopersonsandentitieswithrelationshipswiththeissuer,forwhichtheyreceivedorwillreceivecustomaryfeesandexpenses.WeintendtousethenetproceedsfromthisofferingtoredeemouroutstandingExisting2020NotesandtorepayallamountsoutstandingunderourRevolvingCreditFacility.Affiliatesofcertainoftheunderwritersactasagentsand/orlendersunderourRevolvingCreditFacilityandholdcertainofourExisting2020Notes,andwillreceiveaportionofthenetproceedsofthisofferinginconnectionwiththerepaymentofamountsunderourRevolvingCreditFacilityandtheredemptionoftheExisting2020Notes.

Intheordinarycourseoftheirvariousbusinessactivities,theunderwritersandtheirrespectiveaffiliates,officers,directorsandemployeesmaypurchase,sellorholdabroadarrayofinvestmentsandactivelytradesecurities,derivatives,loans,commodities,currencies,creditdefaultswapsandotherfinancialinstrumentsfortheirownaccountandfortheaccountsoftheircustomers,andsuchinvestmentandtradingactivitiesmayinvolveorrelatetoassets,securitiesand/orinstrumentsoftheissuer(directly,ascollateralsecuringotherobligationsorotherwise)and/orpersonsandentitieswithrelationshipswiththeissuer.Theunderwritersandtheirrespectiveaffiliatesmayalsocommunicateindependentinvestmentrecommendations,marketcolorortradingideasand/orpublishorexpressindependentresearchviewsinrespectofsuchassets,securitiesorinstrumentsandmayatanytimehold,orrecommendtoclientsthattheyshouldacquire,longand/orshortpositionsinsuchassets,securitiesandinstruments.

European Economic Area

PRIIPs Regulation / Prohibition of sales to EEA retail investors —TheNotesarenotintendedtobeoffered,soldorotherwisemadeavailabletoandshouldnotbeoffered,soldorotherwisemadeavailabletoanyretailinvestorintheEuropeanEconomicArea("EEA").Forthesepurposes,aretailinvestormeansapersonwhoisone(ormore)of:(i)aretailclientasdefinedinpoint(11)ofArticle4(1)ofDirective2014/65/EU(asamended,"MiFIDII");or(ii)acustomerwithinthemeaningofDirective2016/97/EU(the"InsuranceDistributionDirective"),wherethatcustomerwouldnotqualifyasaprofessionalclientasdefinedinpoint(10)ofArticle4(1)ofMiFIDII;or(iii)notaqualifiedinvestorasdefinedinDirective2003/71/EC(asamended,the"ProspectusDirective").

S-58

Page 68: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

ConsequentlynokeyinformationdocumentrequiredbyRegulation(EU)No1286/2014(asamended,the"PRIIPsRegulation")forofferingorsellingtheNotesorotherwisemakingthemavailabletoretailinvestorsintheEEAhasbeenpreparedandthereforeofferingorsellingtheNotesorotherwisemakingthemavailabletoanyretailinvestorintheEEAmaybeunlawfulunderthePRIIPSRegulation.

ThisProspectusSupplementhasbeenpreparedonthebasisthatanyofferofNotesinanymemberstateoftheEuropeanEconomicAreawhichhasimplementedtheProspectusDirective(each,a"RelevantMemberState")willbemadepursuanttoanexemptionundertheProspectusDirective,asimplementedinthatRelevantMemberState,fromtherequirementtoproduceaprospectusforoffersoftheNotes.Accordingly,anypersonmakingorintendingtomakeanyofferwithinthatRelevantMemberStateofNotes,whicharethesubjectoftheofferingcontemplatedinthisProspectusSupplement,mayonlydosoincircumstancesinwhichnoobligationarisesfortheIssuerortheunderwriterstoproduceaprospectusforsuchoffer.NeithertheIssuernortheunderwritershaveauthorized,nordotheyauthorize,themakingofanyofferofNotesincircumstancesinwhichanobligationarisesfortheIssuerortheunderwriterstopublishaprospectusforsuchoffer.NeithertheIssuernortheunderwritershaveauthorized,nordotheyauthorize,themakingofanyofferofNotesthroughanyfinancialintermediary,otherthanoffersmadebytheunderwriters,whichconstitutethefinalplacementofNotescontemplatedinthisProspectusSupplement.Theexpression"ProspectusDirective"meansDirective2003/71/EC(andamendmentsthereto,includingthe2010PDAmendingDirective,totheextentimplementedintheRelevantMemberState),andincludesanyrelevantimplementingmeasureintheRelevantMemberStateandtheexpression"2010PDAmendingDirective"meansDirective2010/73/EU.

United Kingdom

EachUnderwriterhasrepresentedandagreedthat:

(a) ithasonlycommunicatedorcausedtobecommunicatedandwillonlycommunicateorcausetobecommunicatedaninvitationorinducementtoengageininvestmentactivity(withinthemeaningofSection21oftheFinancialServicesandMarketsAct2000(FSMA))receivedbyitinconnectionwiththeissueorsaleoftheOfferedNotesincircumstancesinwhichSection21(1)oftheFSMAdoesnotapplytotheIssuersortheGuarantors;and

(b) ithascompliedandwillcomplywithallapplicableprovisionsoftheFSMAwithrespecttoanythingdonebyitinrelationtotheOfferedNotesin,fromorotherwiseinvolvingtheUnitedKingdom.

Hong Kong

TheNotesmaynotbeofferedorsoldinHongKongbymeansofanydocumentotherthan(i)incircumstanceswhichdonotconstituteanoffertothepublicwithinthemeaningoftheCompanies(WindingUpandMiscellaneousProvisions)Ordinance(Cap.32oftheLawsofHongKong)("Companies(WindingUpandMiscellaneousProvisions)Ordinance")orwhichdonotconstituteaninvitationtothepublicwithinthemeaningoftheSecuritiesandFuturesOrdinance(Cap.571oftheLawsofHongKong)("SecuritiesandFuturesOrdinance"),or(ii)to"professionalinvestors"asdefinedintheSecuritiesandFuturesOrdinanceandanyrulesmadethereunder,or(iii)inothercircumstanceswhichdonotresultinthedocumentbeinga"prospectus"asdefinedintheCompanies(WindingUpandMiscellaneousProvisions)Ordinance,andnoadvertisement,invitationordocumentrelatingtotheNotesmaybeissuedormaybeinthepossessionofanypersonforthepurposeofissue(ineachcasewhetherinHongKongorelsewhere),whichisdirectedat,orthecontentsofwhicharelikelytobeaccessedorreadby,thepublicinHongKong(exceptifpermittedtodosounderthesecuritieslawsofHongKong)otherthanwithrespecttoNoteswhichareorareintendedtobe

S-59

Page 69: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

disposedofonlytopersonsoutsideHongKongoronlyto"professionalinvestors"inHongKongasdefinedintheSecuritiesandFuturesOrdinanceandanyrulesmadethereunder.

Singapore

ThisprospectussupplementhasnotbeenregisteredasaprospectuswiththeMonetaryAuthorityofSingapore.Accordingly,thisprospectussupplementandanyotherdocumentormaterialinconnectionwiththeofferorsale,orinvitationforsubscriptionorpurchase,oftheNotesmaynotbecirculatedordistributed,normaytheNotesbeofferedorsold,orbemadethesubjectofaninvitationforsubscriptionorpurchase,whetherdirectlyorindirectly,topersonsinSingaporeotherthan(i)toaninstitutionalinvestor(asdefinedinSection4AoftheSecuritiesandFuturesAct,Chapter289ofSingapore(the"SFA"))underSection274oftheSFA,(ii)toarelevantperson(asdefinedinSection275(2)oftheSFA)pursuanttoSection275(1)oftheSFA,oranypersonpursuanttoSection275(1A)oftheSFA,andinaccordancewiththeconditionsspecifiedinSection275oftheSFAor(iii)otherwisepursuantto,andinaccordancewiththeconditionsof,anyotherapplicableprovisionoftheSFA,ineachcasesubjecttoconditionssetforthintheSFA.

WheretheNotesaresubscribedorpurchasedunderSection275oftheSFAbyarelevantpersonwhichisacorporation(whichisnotanaccreditedinvestor(asdefinedinSection4AoftheSFA))thesolebusinessofwhichistoholdinvestmentsandtheentiresharecapitalofwhichisownedbyoneormoreindividuals,eachofwhomisanaccreditedinvestor,thesecurities(asdefinedinSection239(1)oftheSFA)ofthatcorporationshallnotbetransferablefor6monthsafterthatcorporationhasacquiredtheNotesunderSection275oftheSFAexcept:(1)toaninstitutionalinvestorunderSection274oftheSFAortoarelevantperson(asdefinedinSection275(2)oftheSFA),(2)wheresuchtransferarisesfromanofferinthatcorporation'ssecuritiespursuanttoSection275(1A)oftheSFA,(3)wherenoconsiderationisorwillbegivenforthetransfer,(4)wherethetransferisbyoperationoflaw,(5)asspecifiedinSection276(7)oftheSFA,or(6)asspecifiedinRegulation32oftheSecuritiesandFutures(OffersofInvestments)(SharesandDebentures)Regulations2005ofSingapore("Regulation32").

WheretheNotesaresubscribedorpurchasedunderSection275oftheSFAbyarelevantpersonwhichisatrust(wherethetrusteeisnotanaccreditedinvestor(asdefinedinSection4AoftheSFA))whosesolepurposeistoholdinvestmentsandeachbeneficiaryofthetrustisanaccreditedinvestor,thebeneficiaries'rightsandinterest(howsoeverdescribed)inthattrustshallnotbetransferablefor6monthsafterthattrusthasacquiredtheNotesunderSection275oftheSFAexcept:(1)toaninstitutionalinvestorunderSection274oftheSFAortoarelevantperson(asdefinedinSection275(2)oftheSFA),(2)wheresuchtransferarisesfromanofferthatismadeontermsthatsuchrightsorinterestareacquiredataconsiderationofnotlessthanS$200,000(oritsequivalentinaforeigncurrency)foreachtransaction(whethersuchamountistobepaidforincashorbyexchangeofsecuritiesorotherassets),(3)wherenoconsiderationisorwillbegivenforthetransfer,(4)wherethetransferisbyoperationoflaw,(5)asspecifiedinSection276(7)oftheSFA,or(6)asspecifiedinRegulation32.

Solelyforthepurposesofitsobligationspursuanttosections309B(1)(a)and309B(1)(c)oftheSecuritiesandFuturesAct(Chapter289ofSingapore)(the"SFA"),theIssuerhasdetermined,andherebynotifiesallrelevantpersons(asdefinedinSection309AoftheSFA)thattheNotesare"prescribedcapitalmarketsproducts"(asdefinedintheSecuritiesandFutures(CapitalMarketsProducts)Regulations2018)andExcludedInvestmentProducts(asdefinedinMASNoticeSFA04-N12:NoticeontheSaleofInvestmentProductsandMASNoticeFAA-N16:NoticeonRecommendationsonInvestmentProducts).

S-60

Page 70: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Japan

ThesecuritieshavenotbeenandwillnotberegisteredundertheFinancialInstrumentsandExchangeActofJapan(ActNo.25of1948,asamended),ortheFIEA.Thesecuritiesmaynotbeofferedorsold,directlyorindirectly,inJapanortoorforthebenefitofanyresidentofJapan(includinganypersonresidentinJapanoranycorporationorotherentityorganizedunderthelawsofJapan)ortoothersforreofferingorresale,directlyorindirectly,inJapanortoorforthebenefitofanyresidentofJapan,exceptpursuanttoanexemptionfromtheregistrationrequirementsoftheFIEAandotherwiseincompliancewithanyrelevantlawsandregulationsofJapan.

Canada

TheNotesmaybesoldinCanadaonlytopurchaserspurchasing,ordeemedtobepurchasing,asprincipalthatareaccreditedinvestors,asdefinedinNationalInstrument45-106ProspectusExemptionsorsubsection73.3(1)oftheSecuritiesAct(Ontario),andarepermittedclients,asdefinedinNationalInstrument31-103RegistrationRequirements,ExemptionsandOngoingRegistrantObligations.AnyresaleoftheNotesmustbemadeinaccordancewithanexemptionfrom,orinatransactionnotsubjectto,theprospectusrequirementsofapplicablesecuritieslaws.

SecuritieslegislationincertainprovincesorterritoriesofCanadamayprovideapurchaserwithremediesforrescissionordamagesifthisprospectussupplement(includinganyamendmentthereto)containsamisrepresentation,providedthattheremediesforrescissionordamagesareexercisedbythepurchaserwithinthetimelimitprescribedbythesecuritieslegislationofthepurchaser'sprovinceorterritory.Thepurchasershouldrefertoanyapplicableprovisionsofthesecuritieslegislationofthepurchaser'sprovinceorterritoryforparticularsoftheserightsorconsultwithalegaladvisor.

Pursuanttosection3A.3ofNationalInstrument33-105UnderwritingConflicts(NI33-105),theunderwritersarenotrequiredtocomplywiththedisclosurerequirementsofNI33-105regardingunderwriterconflictsofinterestinconnectionwiththisoffering.

S-61

Page 71: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

VALIDITY OF SECURITIES

ThevalidityoftheNotesofferedherebywillbepasseduponforusbySimpsonThacher&BartlettLLP,NewYork,NewYork.CertainlegalmatterswithrespecttotheofferingoftheNoteswillbepasseduponfortheunderwritersbyLatham&WatkinsLLP,NewYork,NewYork.

EXPERTS

Thefinancialstatementsandmanagement'sassessmentoftheeffectivenessofinternalcontroloverfinancialreporting(whichisincludedinManagement'sReportonInternalControloverFinancialReporting)incorporatedinthisprospectussupplementbyreferencetotheAnnualReportonForm10-KfortheyearendedDecember31,2018havebeensoincorporatedinrelianceonthereportofPricewaterhouseCoopersLLP,anindependentregisteredpublicaccountingfirm,givenontheauthorityofsaidfirmasexpertsinauditingandaccounting.

S-62

Page 72: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

CNO Financial Group, Inc.Debt Securities Common Stock Preferred Stock

Depositary Shares Warrants

Purchase Contracts Units

Wemayofferandsell,fromtimetotime,inoneormoreofferings,anyofthefollowingsecurities:

• debtsecurities,inoneormoreseries,whichmaybeseniordebtsecurities,seniorsubordinateddebtsecuritiesorsubordinateddebtsecurities;

• sharesofourcommonstock;

• sharesofourpreferredstock;

• depositaryshares;

• warrantstopurchaseourdebt,commonorpreferredequitysecurities;

• purchasecontracts;

• units;or

• anycombinationofthesesecurities.

Inaddition,certainsellingstockholdersmay,fromtimetotime,offerandsellsharesofourcommonstockorpreferredstock,ineachcase,inamounts,atpricesandontermsthatwillbedeterminedatthetimeofanysuchoffering.

OurcommonstockislistedontheNewYorkStockExchangeunderthesymbol"CNO."Eachprospectussupplementwillindicateifthesecuritiesofferedtherebywillbelistedonasecuritiesexchange.

Thisprospectusprovidesageneraldescriptionofthesesecurities.Wewillprovidethespecifictermsofthesecurities,includingthenamesofanysellingstockholders,ifapplicable,inoneormoresupplementstothisprospectus.Thisprospectusmaynotbeusedtoofferandsellthesecuritiesunlessaccompaniedbyaprospectussupplement.Youshouldreadthisprospectusandtheapplicableprospectussupplement,aswellasthedocumentsincorporatedbyreferenceinthisprospectusandinanyapplicableprospectussupplement,carefullybeforeyouinvest.

Investing in these securities involves risks. See the information included and incorporated by reference in this prospectusand the applicable prospectus supplement for a discussion of the factors you should carefully consider before deciding topurchase these securities, including the information under "Risk Factors" in our most recent annual report on Form 10-K(as it may be updated in any subsequently filed quarterly reports on Form 10-Q) filed with the Securities and ExchangeCommission.

None of the Securities and Exchange Commission, any state securities commission or any other regulatory body has approved or disapproved ofthese securities or passed upon the adequacy or accuracy of this prospectus. Any representation to the contrary is a criminal offense.

ThedateofthisprospectusisMay10,2018.

Page 73: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

TABLE OF CONTENTS

i

Page ABOUTTHISPROSPECTUS 1WHEREYOUCANFINDMOREINFORMATION 3INCORPORATIONOFCERTAININFORMATIONBYREFERENCE 4FORWARD-LOOKINGSTATEMENTS 5OURCOMPANY 8RISKFACTORS 9RATIOSOFEARNINGSTOFIXEDCHARGES 10USEOFPROCEEDS 11DESCRIPTIONOFDEBTSECURITIES 12DESCRIPTIONOFCAPITALSTOCK 22DESCRIPTIONOFDEPOSITARYSHARES 29DESCRIPTIONOFWARRANTS 32DESCRIPTIONOFPURCHASECONTRACTS 34DESCRIPTIONOFUNITS 34PLANOFDISTRIBUTION 35VALIDITYOFTHESECURITIES 37EXPERTS 37

Page 74: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

ABOUT THIS PROSPECTUS

ThisprospectusisapartofaregistrationstatementthatwefiledwiththeSecuritiesandExchangeCommission(the"SEC")utilizinga"shelf"registrationprocess.Underthisshelfregistrationprocess,wemaysellanycombinationofthesecuritiesdescribedinthisprospectusinoneormoreofferingsfromtimetotime.Inaddition,certainsellingstockholdersmay,fromtimetotime,offerandsellsharesofourcommonstockorpreferredstock,ineachcase,inamounts,atpricesandontermsthatwillbedeterminedatthetimeofanysuchoffering.

Thisprospectusprovidesyouwithageneraldescriptionofthesecuritieswemayoffer.Eachtimewesellsecuritiesunderthisshelfregistrationstatement,wewillprovideaprospectussupplementthatwillcontainspecificinformationaboutthetermsofthatoffering,includingthenamesofanysellingstockholders,ifapplicable,andmayalsoprovideyouwithafreewritingprospectus.Theprospectussupplementandanyfreewritingprospectusmayalsoadd,updateorchangeinformationcontainedinthisprospectus.Wealsoincludeintheprospectussupplementoranyfreewritingprospectuswhereapplicable,informationaboutmaterialUnitedStatesfederalincometaxconsiderationsrelatingtothesecurities.Therefore,ifthereisanyinconsistencybetweentheinformationinthisprospectusandtheprospectussupplementandanyfreewritingprospectus,youshouldrelyontheinformationintheprospectussupplementandanyfreewritingprospectus.Youshouldreadboththisprospectusandanyprospectussupplementandanyfreewritingprospectustogetherwithadditionalinformationdescribedundertheheading"WhereYouCanFindMoreInformation"and"IncorporationofCertainInformationbyReference."

Theexhibitstotheregistrationstatementofwhichthisprospectusisapartcontainthefulltextofcertaincontractsandotherimportantdocumentswehavesummarizedinthisprospectus.Sincethesesummariesmaynotcontainalltheinformationthatyoumayfindimportantindecidingwhethertopurchasethesecuritieswemayoffer,youshouldreviewthefulltextofthesedocuments.TheregistrationstatementandtheexhibitscanbeobtainedfromtheSECasindicatedundertheheading"WhereYouCanFindMoreInformation"below.

Wehavenotauthorizedanydealer,salesmanorotherpersontogiveanyinformationortomakeanyrepresentationotherthanthosecontainedorincorporatedbyreferenceinthisprospectusandanyapplicableprospectussupplementoranyrelatedfreewritingprospectusfiledwiththeSEC.Youmustnotrelyuponanyinformationorrepresentationnotcontainedorincorporatedbyreferenceinthisprospectusortheapplicableprospectussupplement.Thisprospectusandtheapplicableprospectussupplementdonotconstituteanoffertosellorthesolicitationofanoffertobuyanysecuritiesotherthantheregisteredsecuritiestowhichtheyrelate,nordothisprospectusandtheapplicableprospectussupplementconstituteanoffertosellorthesolicitationofanoffertobuysecuritiesinanyjurisdictiontoanypersontowhomitisunlawfultomakesuchofferorsolicitationinsuchjurisdiction.

Youshouldnotassumethattheinformationcontainedinthisprospectusandtheapplicableprospectussupplementisaccurateonanydatesubsequenttothedatesetforthonthefrontofthedocumentorthatanyinformationwehaveincorporatedbyreferenceiscorrectonanydatesubsequenttothedateofthedocumentincorporatedbyreference,eventhoughthisprospectusandanyapplicableprospectussupplementisdeliveredorsecuritiesaresoldonalaterdate.Ourbusiness,financialcondition,resultsofoperationsandprospectsmayhavechangedsincethosedates.

Asusedinthisprospectus,unlessotherwisespecifiedorunlessthecontextindicatesotherwise,referencesinthisprospectusto:

• "CNO"orthe"holdingcompany"referonlytoCNOFinancialGroup,Inc.onanunconsolidatedbasis.PriortoitsnamechangeinMay2010,CNOwasformerlyknownasConseco,Inc.,aDelawarecorporation.CNObecamethesuccessortoConseco,Inc.,anIndiana

1

Page 75: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

corporation(our"Predecessor"),inconnectionwithourbankruptcyreorganizationwhichbecameeffectiveonSeptember10,2003;and

• "CNOFinancialGroup,"the"Company,""we,""us,"and"our"refertoCNOanditssubsidiariesonaconsolidatedbasisor,whenthecontextrequiresotherwise,ourPredecessoranditssubsidiariesonaconsolidatedbasis.

Referencesto"thisprospectus"refertothisprospectusandanyapplicableprospectussupplement.

2

Page 76: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

WHERE YOU CAN FIND MORE INFORMATION

CNOfilesreports,proxystatementsandotherinformationwiththeSEC.Thesereports,proxystatementsandotherinformationcanbereadandcopiedattheSEC'spublicreferenceroomat100FStreet,N.E.,Washington,D.C.20549.PleasecalltheSECat1-800-SEC-0330forfurtherinformationontheoperationofthepublicreferenceroom.TheSECmaintainsaninternetsiteatwww.sec.govthatcontainsreports,proxyandinformationstatementsandotherinformationregardingcompaniesthatfileelectronicallywiththeSEC,includingCNO.CNO'scommonstockislistedandtradingontheNewYorkStockExchange(the"NYSE")underthesymbol"CNO."Thesereports,proxystatementsandotherinformationcanalsobereadattheofficesoftheNYSE,11WallStreet,NewYork,NewYork10005.

WehavefiledwiththeSECaregistrationstatementonFormS-3withrespecttothesecuritiescoveredbythisprospectus.Thisprospectus,filedasapartoftheregistrationstatement,doesnotcontainalltheinformationsetforthintheregistrationstatementanditsexhibits,partsofwhichareomittedinaccordancewiththerulesandregulationsoftheSEC.Forfurtherinformationwithrespecttousandthesecuritiescoveredbythisprospectus,referenceismadetotheregistrationstatementandtotheexhibits.Statementsinthisprospectusaboutthecontentsofanycontract,agreementorotherdocumentarenecessarilynotcompleteand,ineachinstance,wereferyoutothecopyofsuchcontract,agreementordocumentfiledasanexhibittotheregistrationstatement,witheachsuchstatementbeingqualifiedinallrespectbyreferencetothedocumenttowhichitrefers.

3

Page 77: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

INCORPORATION OF CERTAIN INFORMATION BY REFERENCE

Inthisprospectus,CNO"incorporatesbyreference"theinformationthatitfileswiththeSEC,whichmeansthatCNOcandiscloseimportantinformationtoyoubyreferringyoutoadocumentthatitfiledwiththeSEC.Theinformationsoincorporatedbyreferenceisconsideredtobeapartofthisprospectus,andinformationthatCNOfileslaterwiththeSECwillautomaticallyupdateandsupersedethisinformation.Anyinformationcontainedinthisprospectusupdatesand,whereapplicable,supersedestheinformationinthedocumentsincorporatedbyreferencehereinlistedbelow.CNOincorporatesbyreferencethedocumentslistedbelowandanyfilingsmadewiththeSECunderSections13(a),13(c),14or15(d)oftheSecuritiesExchangeActof1934,asamended(the"ExchangeAct")(excludinganyCurrentReportsonForm8-KcontaininganydisclosurepursuanttoItem2.02orItem7.01unlessotherwiseindicated),afterthedateofthisprospectusanduntilthesettlementoftheoffering(s)towhichthisprospectusrelates:

• AnnualReportonForm10-KfortheyearendedDecember31,2017(includingportionsofourDefinitiveProxyStatementonSchedule14AfiledonMarch28,2018thatareincorporatedbyreferenceintoPartIIIofour2017Form10-K);

• QuarterlyReportonForm10-QforthequarterendedMarch31,2018;and

• CurrentReportonForm8-KfiledonMay9,2018(excludingItem7.01andrelatedExhibit99.1).

Anystatementcontainedinadocumentincorporatedordeemedtobeincorporatedbyreferenceinthisprospectuswillbedeemedtobemodifiedorsupersededtotheextentthatastatementcontainedhereinorinanyothersubsequentlyfileddocumentwhichalsoisorisdeemedtobeincorporatedbyreferenceinthisprospectusmodifiesorsupersedesthatstatement.Anystatementsomodifiedorsupersededwillnotbedeemed,exceptassomodifiedorsuperseded,toconstituteapartofthisprospectus.

CNOwillprovidewithoutchargeuponwrittenororalrequest,acopyofanyorallofthedocumentsthatareincorporatedbyreferenceintothisprospectus,otherthanexhibitstothosedocuments,unlessthoseexhibitsarespecificallyincorporatedbyreferenceintothosedocuments.RequestsshouldbedirectedtoCNOatInvestorRelations,CNOFinancialGroup,Inc.,11825N.PennsylvaniaStreet,Carmel,Indiana46032,phonenumber(317)817-2893.YoumayalsoobtainthedocumentsincorporatedbyreferenceintothisprospectusasofthedatehereofatCNO'swebsite,www.cnoinc.com.AllotherinformationcontainedonoraccessiblethroughCNO'swebsiteisnotapartofthisdocument.

4

Page 78: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

FORWARD-LOOKING STATEMENTS

Ourstatements,trendanalysesandotherinformationcontainedinthisprospectusandthedocumentsincorporatedbyreferencecontainforward-lookingstatementswithinthemeaningofthefederalsecuritieslawsandthePrivateSecuritiesLitigationReformActof1995.Forward-lookingstatementstypicallyareidentifiedbytheuseoftermssuchas"anticipate,""believe,""plan,""estimate,""expect,""project,""intend,""may,""will,""would,""contemplate,""possible,""attempt,""seek,""should,""could,""goal,""target,""ontrack,""comfortablewith,""optimistic,""guidance,""outlook"andsimilarwords,althoughsomeforward-lookingstatementsareexpresseddifferently.Youshouldconsiderstatementsthatcontainthesewordscarefullybecausetheydescribeourexpectations,plans,strategiesandgoalsandourbeliefsconcerningfuturebusinessconditions,ourresultsofoperations,financialposition,andourbusinessoutlookortheystateother"forward-looking"informationbasedoncurrentlyavailableinformation.The"RiskFactors"sectionofourAnnualReportonForm10-KfortheyearendedDecember31,2017,whichisincorporatedbyreferenceintothisprospectus,providesexamplesofrisks,uncertaintiesandeventsthatcouldcauseouractualresultstodiffermateriallyfromtheexpectationsexpressedinourforward-lookingstatements.Assumptionsandotherimportantfactorsthatcouldcauseouractualresultstodiffermateriallyfromthoseanticipatedinourforward-lookingstatementsinclude,amongotherthings:

• changesinorsustainedlowinterestratescausingreductionsininvestmentincome,themarginsofourfixedannuityandlifeinsurancebusinesses,andsalesof,anddemandfor,ourproducts;

• expectationsoflowerfutureinvestmentearningsmaycauseustoaccelerateamortization,writedownthebalanceofinsuranceacquisitioncostsorestablishadditionalliabilitiesforinsuranceproducts;

• generaleconomic,marketandpoliticalconditionsanduncertainties,includingtheperformanceandfluctuationsofthefinancialmarketswhichmayaffectthevalueofourinvestmentsaswellasourabilitytoraisecapitalorrefinanceexistingindebtednessandthecostofdoingso;

• theultimateoutcomeoflawsuitsfiledagainstusandotherlegalandregulatoryproceedingstowhichwearesubject;

• ourabilitytomakeanticipatedchangestocertainnon-guaranteedelementsofourlifeinsuranceproducts;

• ourabilitytoobtainadequateandtimelyrateincreasesonourhealthproducts,includingourlong-termcarebusiness;

• thereceiptofanyrequiredregulatoryapprovalsfordividendandsurplusdebentureinterestpaymentsfromourinsurancesubsidiaries;

• mortality,morbidity,theincreasedcostandusageofhealthcareservices,persistency,theadequacyofourpreviousreserveestimatesandotherfactorswhichmayaffecttheprofitabilityofourinsuranceproducts;

• changesinourassumptionsrelatedtodeferredacquisitioncostsorthepresentvalueoffutureprofits;

• therecoverabilityofourdeferredtaxassetsandtheeffectofpotentialownershipchangesandtaxratechangesontheirvalue;

• changestoourestimatesoftheimpactofcomprehensivefederaltaxlegislationrelatedtotheTaxCutsandJobsAct;

• ourassumptionthatthepositionswetakeonourtaxreturnfilingswillnotbesuccessfullychallengedbytheInternalRevenueService;

5

Page 79: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

• changesinaccountingprinciplesandtheinterpretationthereof;

• ourabilitytocontinuetosatisfythefinancialratioandbalancerequirementsandothercovenantsofourdebtagreements;

• ourabilitytoachieveanticipatedexpensereductionsandlevelsofoperationalefficienciesincludingimprovementsinclaimsadjudicationandcontinuedautomationandrationalizationofoperatingsystems;

• performanceandvaluationofourinvestments,includingtheimpactofrealizedlosses(includingother-than-temporaryimpairmentcharges);

• ourabilitytoidentifyproductsandmarketsinwhichwecancompeteeffectivelyagainstcompetitorswithgreatermarketshare,higherratings,greaterfinancialresourcesandstrongerbrandrecognition;

• ourabilitytogeneratesufficientliquiditytomeetourdebtserviceobligationsandothercashneeds;

• changesincapitaldeploymentopportunities;

• ourabilitytomaintaineffectivecontrolsoverfinancialreporting;

• ourabilitytocontinuetorecruitandretainproductiveagentsanddistributionpartners;

• customerresponsetonewproducts,distributionchannelsandmarketinginitiatives;

• ourabilitytoachieveadditionalupgradesofthefinancialstrengthratingsofCNOandourinsurancecompanysubsidiariesaswellastheimpactofourratingsonourbusiness,ourabilitytoaccesscapital,andthecostofcapital;

• regulatorychangesoractions,includingthoserelatingtoregulationofthefinancialaffairsofourinsurancecompanies,suchasthecalculationofrisk-basedcapitalandminimumcapitalrequirements,andpaymentofdividendsandsurplusdebentureinteresttous;regulationofthesale,underwritingandpricingofproducts;andhealthcareregulationaffectinghealthinsuranceproducts;

• changesintheFederalincometaxlawsandregulationswhichmayaffectoreliminatetherelativetaxadvantagesofsomeofourproductsoraffectthevalueofourdeferredtaxassets;

• availabilityandeffectivenessofreinsurancearrangements,aswellastheimpactofanydefaultsorfailureofreinsurerstoperform;

• theamountwemayneedtopaytoareinsurerandtheearningschargewemayincurinconnectionwithalong-termcarereinsurancetransaction;

• theperformanceofthirdpartyserviceprovidersandpotentialdifficultiesarisingfromoutsourcingarrangements;

• thegrowthrateofsales,collectedpremiums,annuitydepositsandassets;

• interruptionintelecommunication,informationtechnologyorotheroperationalsystemsorfailuretomaintainthesecurity,confidentialityorprivacyofsensitivedataonsuchsystems;

• eventsofterrorism,cyberattacks,naturaldisastersorothercatastrophicevents,includinglossesfromadiseasepandemic;

• ineffectivenessofriskmanagementpoliciesandproceduresinidentifying,monitoringandmanagingrisks;and

• theriskfactorsoruncertaintieslistedfromtimetotimeinourfilingswiththeSEC.

6

Page 80: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Otherfactorsandassumptionsnotidentifiedabovearealsorelevanttotheforward-lookingstatements,andiftheyproveincorrect,couldalsocauseactualresultstodiffermateriallyfromthoseprojected.

Allwrittenororalforward-lookingstatementsattributabletousareexpresslyqualifiedintheirentiretybytheforegoingcautionarystatement.Ourforward-lookingstatementsspeakonlyasofthedatemade.Weassumenoobligationtoupdateortopubliclyannouncetheresultsofanyrevisionstoanyoftheforward-lookingstatementstoreflectactualresults,futureeventsordevelopments,changesinassumptionsorchangesinotherfactorsaffectingtheforward-lookingstatements.

7

Page 81: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

OUR COMPANY

CNOisaholdingcompanyforagroupofinsurancecompaniesoperatingthroughouttheUnitedStatesthatdevelop,marketandadministerhealthinsurance,annuity,individuallifeinsuranceandotherinsuranceproducts.

Wefocusonservingmiddle-incomepre-retireeandretiredAmericans,whichwebelieveareattractive,underserved,highgrowthmarkets.Wesellourproductsthroughthreedistributionchannels:careeragents,independentproducers(someofwhomselloneormoreofourproductlinesexclusively)anddirectmarketing.

TheCompanymanagesitsbusinessthroughthefollowingoperatingsegments:BankersLife,WashingtonNationalandColonialPenn,whicharedefinedonthebasisofproductdistribution;andcorporateoperations,comprisedofholdingcompanyactivitiesandcertainnoninsurancecompanybusinesses.Inthefourthquarterof2016,webeganreportingthelong-termcareblockrecapturedfromBeechwoodReLtd.effectiveSeptember30,2016,asanadditionalbusinesssegment.

Ourinsurancesegmentsaredescribedbelow:

• BankersLife,whichmarketsanddistributesMedicaresupplementinsurance,interest-sensitivelifeinsurance,traditionallifeinsurance,fixedannuitiesandlong-termcareinsuranceproductstothemiddle-incomeseniormarketthroughadedicatedfieldforceofcareeragents,financialandinvestmentadvisors,andsalesmanagerssupportedbyanetworkofcommunity-basedsalesoffices.TheBankersLifesegmentincludesprimarilythebusinessofBankersLifeandCasualtyCompany.BankersLifealsohasvariousdistributionandmarketingagreementswithotherinsurancecompaniestouseBankersLife'scareeragentstodistributeMedicareAdvantageandprescriptiondrugplanproductsinexchangeforafee.

• WashingtonNational,whichmarketsanddistributessupplementalhealth(includingspecifieddisease,accidentandhospitalindemnityinsuranceproducts)andlifeinsurancetomiddle-incomeconsumersathomeandattheworksite.TheseproductsaremarketedthroughPerformanceMattersAssociates,Inc.,awhollyownedsubsidiary,andthroughindependentmarketingorganizationsandinsuranceagenciesincludingworksitemarketing.TheproductsbeingmarketedareunderwrittenbyWashingtonNationalInsuranceCompany("WashingtonNational").Thissegment'sbusinessalsoincludescertainclosedblocksofannuitiesandMedicaresupplementpolicieswhicharenolongerbeingactivelymarketedbythissegmentandwereprimarilyissuedoracquiredbyWashingtonNational.

• ColonialPenn,whichmarketsprimarilygradedbenefitandsimplifiedissuelifeinsurancedirectlytocustomersintheseniormiddle-incomemarketthroughtelevisionadvertising,directmail,theinternetandtelemarketing.TheColonialPennsegmentincludesprimarilythebusinessofColonialPennLifeInsuranceCompany.

• Long-termcareinrun-offconsistsofthelong-termcarebusinessthatwasrecapturedduetotheterminationofcertainreinsuranceagreementseffectiveSeptember30,2016.ThisbusinessisnotactivelymarketedandwasissuedoracquiredbyWashingtonNationalandBankersConsecoLifeInsuranceCompany.

OurcommonstockispubliclytradedontheNewYorkStockExchangeunderthesymbol"CNO."

CNOisacorporationorganizedunderthelawsoftheStateofDelaware.Ourprincipalexecutiveofficesarelocatedat11825N.PennsylvaniaStreet,Carmel,Indiana46032,andourtelephonenumberis(317)817-6100.Ourwebsiteiswww.CNOinc.com.Informationonoraccessiblethroughourwebsiteisnotpartofthisprospectusoranyprospectussupplement.

8

Page 82: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

RISK FACTORS

Ourbusinessissubjecttouncertaintiesandrisks.Beforedecidingwhethertopurchaseanyofoursecurities,youshouldcarefullyconsiderandevaluatealloftheinformationincludedandincorporatedbyreferenceinthisprospectus,includingtheriskfactorsincorporatedbyreferencefromourmostrecentannualreportonForm10-K,asupdatedbyourquarterlyreportsonForm10-QandotherfilingswemakewiththeSEC.Ourbusiness,financialcondition,liquidity,resultsofoperationsorprospectscouldbemateriallyadverselyaffectedbyanyoftheserisksandcouldresultinapartialorcompletelossofyourinvestment.

9

Page 83: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

RATIOS OF EARNINGS TO FIXED CHARGES

Thefollowingtablesetsforthourratiosofearningstofixedchargesfortheperiodsindicated.Thisinformationshouldbereadinconjunctionwiththeconsolidatedfinancialstatementsandtheaccompanyingnotesincorporatedbyreferenceinthisprospectus.Duringtheperiodsindicated,wehadnooutstandingsharesofpreferredstock,andaccordingly,ourratioofearningstofixedchargesisthesameasourratioofearningstofixedchargesandpreferreddividendsforallperiodsindicated.

Earningsavailableforfixedchargesconsistofpre-taxincomefromoperationsandfixedcharges.Fixedchargesconsistofinterestexpenseoncorporatedebt,interestexpenseoninvestmentborrowingsandborrowingsrelatedtovariableinterestentities,interestaddedtopolicyholderaccountbalancesandtheinterestportionofrentalexpense(whichisestimatedtobe33%ofrentalexpense).

10

Year Ended December 31,

Three Months Ended

March 31, 2018

2013 2014 2015 2016 2017 Ratioofearningstofixedcharges 1.87x 1.62x 2.59x 2.43x 2.94x 2.71x

Page 84: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

USE OF PROCEEDS

Unlessweotherwisestateintheapplicableprospectussupplement,weintendtousethenetproceedsfromthesaleofthesecuritiesforgeneralcorporatepurposes.Generalcorporatepurposesmayincluderepaymentofdebt,additionstoworkingcapital,capitalexpenditures,investmentsinoursubsidiaries,possibleacquisitionsandtherepurchase,redemptionorretirementofsecurities,includingsharesofourcommonstock.Thenetproceedsmaybetemporarilyinvestedorappliedtorepayshort-termorrevolvingdebtpriortouse.Inthecaseofasaleofourcommonstockbyanysellingstockholders,wewillnotreceiveanyoftheproceedsfromsuchasale.

11

Page 85: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

DESCRIPTION OF DEBT SECURITIES

Thefollowingisasummaryofthegeneraltermsofthedebtsecuritiesandthematerialprovisionsoftheindenturefiledasanexhibittotheregistrationstatementofwhichthisprospectusisapart.Wewillfileaprospectussupplementthatmaycontainadditionaltermswhenweissuedebtsecurities.Thetermspresentedhere,togetherwiththetermsinarelatedprospectussupplement,willbeadescriptionofthematerialtermsofthedebtsecurities.YoushouldalsoreadtheindenturebetweenusandU.S.BankNationalAssociation,astrusteeunderwhichthedebtsecuritieswillbeissued.WehavefiledtheindenturegoverningdebtsecuritieswiththeSECasanexhibittotheregistrationstatementofwhichthisprospectusisapart.Allcapitalizedtermshavethemeaningsspecifiedintheindenture.

Wemayissue,fromtimetotime,debtsecurities,inoneormoreseries,thatwillconsistofeitherourseniordebt,ourseniorsubordinateddebtoroursubordinateddebt.Werefertothesubordinateddebtsecuritiesandtheseniorsubordinateddebtsecuritiestogetherasthesubordinatedsecurities.Debtsecurities,whethersenior,seniorsubordinatedorsubordinated,maybeissuedasconvertibledebtsecuritiesorexchangeabledebtsecurities.

Foreachseriesofdebtsecurities,theapplicableprospectussupplementfortheseriesmaychangeandsupplementthesummarybelow.

General Terms of the Indenture

Theindenturedoesnotlimittheamountofdebtsecuritiesthatwemayissue.Itprovidesthatwemayissuedebtsecuritiesuptotheprincipalamountthatwemayauthorizeandmaybeinanycurrencyorcurrencyunitthatwemaydesignate.Exceptforthelimitationsonconsolidation,mergerandsaleofallorsubstantiallyallofourassetscontainedintheindenture(see"—Consolidation,MergerorSale"below),thetermsoftheindenturedonotcontainanycovenantsorotherprovisionsdesignedtogiveholdersofanydebtsecuritiesprotectionagainstchangesinouroperations,financialconditionortransactionsinvolvingus.Wemayissuethedebtsecuritiesissuedundertheindentureas"discountsecurities,"whichmeanstheymaybesoldatadiscountbelowtheirstatedprincipalamount.Thesedebtsecurities,aswellasotherdebtsecuritiesthatarenotissuedatadiscount,maybeissuedwith"originalissuediscount,"orOID,forU.S.federalincometaxpurposesbecauseofinterestpaymentandothercharacteristicsortermsofthedebtsecurities.CertainU.S.federalincometaxconsiderationsapplicabletodebtsecuritiesissuedwithOIDwillbedescribedinmoredetailinanyapplicableprospectussupplement.

Theapplicableprospectussupplementforaseriesofdebtsecuritiesthatweissuewilldescribe,amongotherthings,thefollowingtermsoftheoffereddebtsecurities:

• thetitleoftheseriesofdebtsecurities;

• thepriceorprices(expressedasapercentageoftheprincipalamount)atwhichwewillsellthedebtsecurities;

• anylimitontheaggregateprincipalamountoftheseriesofdebtsecurities;

• whetherthedebtsecuritiesrankasseniordebt,seniorsubordinateddebtorsubordinateddebtoranycombinationthereof,andthetermsofanysubordination;

• thetermsandconditions,ifany,uponwhichtheseriesofdebtsecuritieswillbeconvertibleintoorexchangeableforothersecurities;

• whethersecuritiesissuedbyuswillbesecuredorunsecured,andifsecured,whatthecollateralwillconsistof;

• thematuritydate(s);

12

Page 86: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

• therateorrates(whichmaybefixedorvariable)perannumorthemethodusedtodeterminetherateorrates(includinganycurrencyexchangerate,commodity,commodityindex,stockexchangeindexorfinancialindex)atwhichthedebtsecuritieswillbearinterest,thedateordatesfromwhichinterestwillaccrueorthemethodfordeterminingdatesfromwhichinterestwillaccrue,thedateordatesonwhichinterestwillcommenceandbepayableandanyregularrecorddatefortheinterestpayableonanyinterestpaymentdate;

• themannerinwhichtheamountsofpaymentofprincipalof,premium,ifany,orinterest,ifany,ontheseriesofdebtsecuritieswillbedetermined(ifsuchamountsmaybedeterminedbyreferencetoanindexbasedonacurrencyorcurrenciesorbyreferencetoacurrencyexchangerate,commodity,commodityindex,stockexchangeindexorfinancialindex);

• theplaceorplaceswhereprincipalof,premium,ifany,andinterest,ifany,onthedebtsecuritieswillbepayableandthemethodofsuchpayment,ifbywiretransfer,mailorothermeans;

• provisionsrelatedtoredemptionorearlyrepaymentofthedebtsecuritiesofouroption;

• provisionsrelatedtonoticeofredemption,whichsuchnoticemay,atourdiscretion,besubjecttosatisfactionofoneormoreconditionsprecedent(including,butnotlimitedto,thecompletionofatransactionoraneventsuchasanequityoffering,debtofferingorchangeofcontroloftheCompany);

• ourobligation,ifany,toredeemorpurchaseanyseriesofdebtsecuritiespursuanttoanysinkingfundoranalogousprovisionsorattheoptionofaholderthereofandtheperiodorperiodswithinwhich,thepriceorpricesatwhichandthetermsandconditionsuponwhichsuchdebtsecuritiesshallberedeemedorpurchased,inwholeorinpart,pursuanttosuchobligation;

• theauthorizeddenominations;

• theformofthedebtsecuritiesandwhetherthedebtsecuritieswillbeissuedindefinitiveorfullyregisteredform(andifinfullyregisteredform,whetherthedebtsecuritieswillbeissuable,inwholeorinpart,asglobaldebtsecurities);

• anydepositaries,interestratecalculationagents,bidsolicitationagents,conversionorexchangeagents,exchangeratecalculationagentsorotheragentswithrespecttothedebtsecurities;

• anychangesinthetrusteeforsuchdebtsecurities;

• theportionofprincipalamountofthedebtsecuritiespayableupondeclarationofaccelerationofthematuritydate,ifotherthantheprincipalamount;

• anychangesinoradditionstothecovenantsapplicabletotheparticulardebtsecuritiesbeingissued,including,amongothers,theconsolidation,mergerorsalecovenant;

• additionstoorchangesintheEventsofDefaultwithrespecttothesecuritiesandanychangeintherightofthetrusteeortheholderstodeclaretheprincipal,premium,ifany,andinterest,ifany,withrespecttosuchsecuritiestobedueandpayable;

• thecurrencyofdenominationofthedebtsecurities;

• thedesignationofthecurrency,currenciesorcurrencyunitsinwhichthepurchasepricefor,theprincipalofandanypremiumandanyintereston,suchsecuritieswillbepayable;

• ifpaymentsofprincipalof,premium,ifany,orinterest,ifany,onthedebtsecuritieswillbemadeinoneormorecurrenciesorcurrencyunitsotherthanthatorthoseinwhichthedebtsecuritiesaredenominated,themannerinwhichtheexchangeratewithrespecttothesepaymentswillbedetermined;

13

Page 87: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

• whetheranyunderwriter(s)willactasmarketmaker(s)forthedebtsecurities;

• theextenttowhichasecondarymarketforthedebtsecuritiesisexpectedtodevelop;

• additionstoorchangesinordeletionsoftheprovisionsrelatingtocovenantdefeasanceandlegaldefeasance;

• additionstoorchangesintheprovisionsrelatingtosatisfactionanddischargeoftheindenture;

• additionstoorchangesintheprovisionsrelatingtothemodificationoftheindenturebothwithandwithouttheconsentofholdersofdebtsecuritiesissuedundertheindenture;and

• anyothertermsofthedebtsecurities,whichmaymodify,supplementordeleteanyprovisionoftheindentureasitappliestothatseries.

TheapplicableprospectussupplementwilldiscusscertainU.S.federalincometaxconsiderationsforholdersofanydebtsecurities,ifany,andthesecuritiesexchangeorquotationsystemonwhichanydebtsecuritiesaretobelistedorquoted,ifany.

Conversion or Exchange Rights

Debtsecuritiesmaybeconvertibleintoorexchangeableforothersecurities,including,forexample,sharesofourequitysecurities.Thetermsandconditionsofconversionorexchangewillbestatedintheapplicableprospectussupplement.Thetermswillinclude,amongothers,thefollowing:

• theconversionorexchangerateandconversionorexchangeprice;

• theconversionorexchangeperiod;

• provisionsregardingtheabilityofusortheholdertoconvertorexchangethedebtsecurities;

• eventsrequiringadjustmenttotheconversionorexchangerate;and

• provisionsaffectingconversionorexchangeintheeventofourredemptionofthedebtsecurities.

Consolidation, Merger or Sale

Wecannotconsolidateormergewithorinto,orsell,lease,transferorotherwisedisposeofallorsubstantiallyallofourassetsto,anyperson,andwecannotpermitanyotherpersontoconsolidatewithormergeintous,unless(1)wewillbethecontinuingentityor(2)thesuccessorpersonisacorporation,trust,limitedliabilitycompany,partnershiporotherentityorganizedunderthelawsoftheUnitedStatesoranyStatethereofortheDistrictofColumbiathatexpresslyassumesourobligationsundereachseriesofdebtsecuritiesandtheindenture.Inaddition,wecannotcompletesuchtransactionunlessimmediatelyaftercompletingthetransaction,noEventofDefault(asdefinedbelow)undertheindenture,andnoeventwhich,afternoticeorlapseoftimeorboth,wouldbecomeanEventofDefaultundertheindenture,shallhaveoccurredandbecontinuing.Whenthesuccessorpersonhasassumedourobligationsunderthedebtsecuritiesandtheindenture,weshallnotbedischargedfromallourobligationsunderthedebtsecuritiesandtheindentureexceptinthecaseofthesaleofallofourassets.

Thiscovenantwouldnotapplytoanyrecapitalizationtransaction,achangeofcontrolofusorahighlyleveragedtransaction,unlessthetransactionorchangeofcontrolwerestructuredtoincludeamergerorconsolidationorsale,leaseortransferorotherdispositionofallorsubstantiallyallofourassets.

Theapplicableprospectussupplementwilldescribeanymodificationsofthiscovenant.

14

Page 88: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Events of Default

Theterm"EventofDefault,"whenusedintheindenturewithrespecttoanyseriesofdebtsecurities,unlessotherwiseindicatedintheapplicableprospectussupplement,meansanyofthefollowing:

• failuretopayinterestfor30daysafterthedatepaymentisdueandpayable;

• failuretopayprincipalorpremium,ifany,onanydebtsecuritywhendue,eitheratmaturity,uponanyredemption,uponanyrepurchase,bydeclarationorotherwise;

• failuretomakesinkingfundpayments,ifany,whendueinrespectofthatseries;

• failuretoperformothercovenants(otherthanacovenantthathasbeenincludedintheindenturesolelyforthebenefitofaseriesofdebtsecuritiesotherthanthatseries)for60daysafternoticethatperformancewasrequired;

• certaineventsinbankruptcyorinsolvencyrelatingtous;or

• anyotherEventofDefaultprovidedintheapplicableofficers'certificate,resolutionofourboardofdirectorsorthesupplementalindentureunderwhichweissueaseriesofdebtsecurities.

AnEventofDefaultforaparticularseriesofdebtsecuritiesdoesnotnecessarilyconstituteanEventofDefaultforanyotherseriesofdebtsecuritiesissuedundertheindenture.

IfanEventofDefaultwithrespecttoanyseriesofdebtsecuritiesoccursandiscontinuing,theneitherthetrusteeforsuchseriesortheholdersofamajorityinaggregateprincipalamountoftheoutstandingdebtsecuritiesofsuchseries,bynoticeinwriting,maydeclaretheprincipalamount(or,ifthedebtsecuritiesarediscountsecurities,thatportionoftheprincipalamountasmaybespecifiedinthetermsofthatseries)ofandinterestonallofthedebtsecuritiesofsuchseriestobedueandpayableimmediately.WereferyoutotheapplicableprospectussupplementrelatingtoanyseriesofdebtsecuritiesthatarediscountsecuritiesfortheparticularprovisionsrelatingtoaccelerationofaportionoftheprincipalamountofsuchdiscountsecuritiesupontheoccurrenceofanEventofDefault.

Theholdersofnotlessthanamajorityinaggregateprincipalamountofthedebtsecuritiesofeachaffectedseriesmay,aftersatisfyingcertainconditions,rescindandannulanyoftheabove-describeddeclarationsandconsequencesinvolvingsuchseries.

IfanEventofDefaultrelatingtocertaineventsinourbankruptcyorinsolvencyoccursandiscontinuing,thentheprincipalamount(or,ifthedebtsecuritiesarediscountsecurities,thatportionoftheprincipalamountasmaybespecifiedinthetermsofthatseries)ofallofthedebtsecuritiesoutstanding,andanyaccruedinterest,willautomaticallybecomedueandpayableimmediately,withoutanydeclarationorotheractbythetrusteeoranyholder.

Theindentureimposeslimitationsonsuitsbroughtbyholdersofdebtsecuritiesagainstus.Exceptforactionsforpaymentofoverdueprincipalorinterest,noholderofdebtsecuritiesofanyseriesmayinstituteanyactionagainstusundertheindentureunless:

• theholderhaspreviouslygiventothetrusteewrittennoticeofdefaultandcontinuanceofsuchdefault;

• theholdersofnotlessthanamajorityinprincipalamountoftheoutstandingdebtsecuritiesofthatserieshaverequestedthatthetrusteeinstitutetheaction;

• therequestingholdershaveofferedthetrusteeindemnityandsecuritysatisfactorytoitforexpensesandliabilitiesthatmaybeincurredbybringingtheactionsatisfactorytothetrustee;

• thetrusteehasnotinstitutedtheactionwithin60daysoftherequest;and

15

Page 89: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

• thetrusteehasnotreceivedinconsistentdirectionbytheholdersofamajorityinprincipalamountofthatseriesofdebtsecurities.

Wewillberequiredtofileannuallywiththetrusteeacertificate,signedbyoneofourofficers,statingwhetherornottheofficerknowsofanydefaultbyusintheperformance,observanceorfulfillmentofanyconditionorcovenantoftheindenture.Inaddition,wewillberequiredtonotifythetrusteeinwritingwithin30daysfollowingknowledgeoftheoccurrenceofanysuchdefault.

Transfer and Exchange

Unlessotherwisestatedintheapplicableprospectussupplement,eachdebtsecuritywillberepresentedbyeitheroneormoreglobalsecuritiesregisteredinthenameofTheDepositoryTrustCompany,asdepositary,oranominee(wewillrefertoanydebtsecurityrepresentedbyaglobaldebtsecurityasa"book-entrydebtsecurity"),oracertificateissuedindefinitiveregisteredform(wewillrefertoanydebtsecurityrepresentedbyacertificatedsecurityasa"certificateddebtsecurity")assetforthintheapplicableprospectussupplement.Exceptassetforthunderthesubheading"—GlobalDebtSecuritiesandBook-EntrySystem"below,book-entrydebtsecuritieswillnotbeissuableincertificatedform.

GlobalDebtSecuritiesandBook-EntrySystem.Eachglobaldebtsecurityrepresentingbook-entrydebtsecuritieswillbedepositedwith,oronbehalfof,thedepositary,andregisteredinthenameofthedepositaryoranomineeofthedepositary.

Weanticipatethatthedepositarywillfollowthefollowingprocedureswithrespecttobook-entrydebtsecurities.

Ownershipofbeneficialinterestsinbook-entrydebtsecuritieswillbelimitedtopersonsthathaveaccountswiththedepositaryfortherelatedglobaldebtsecurity,whichwerefertoasparticipants,orpersonsthatmayholdintereststhroughparticipants.Upontheissuanceofaglobaldebtsecurity,thedepositarywillcredit,onitsbook-entryregistrationandtransfersystem,theparticipants'accountswiththerespectiveprincipalamountsofthebook-entrydebtsecuritiesrepresentedbysuchglobaldebtsecuritybeneficiallyownedbysuchparticipants.Theaccountstobecreditedwillbedesignatedbyanydealers,underwritersoragentsparticipatinginthedistributionofthebook-entrydebtsecurities.Ownershipofbook-entrydebtsecuritieswillbeshownon,andthetransferofsuchownershipinterestswillbeeffectedonlythrough,recordsmaintainedbythedepositaryfortherelatedglobaldebtsecurity(withrespecttointerestsofparticipants)andontherecordsofparticipants(withrespecttointerestsofpersonsholdingthroughparticipants).Thelawsofsomestatesmayrequirethatcertainpurchasersofsecuritiestakephysicaldeliveryofsuchsecuritiesindefinitiveform.Theselawsmayimpairtheabilitytoown,transferorpledgebeneficialinterestsinbook-entrydebtsecurities.

Solongasthedepositaryforaglobaldebtsecurity,oritsnominee,istheregisteredownerofthatglobaldebtsecurity,thedepositaryoritsnominee,asthecasemaybe,willbeconsideredthesoleownerorholderofthebook-entrydebtsecuritiesrepresentedbysuchglobaldebtsecurityforallpurposesundertheindenture.Exceptasdescribedbelow,beneficialownersofbook-entrydebtsecuritieswillnotbeentitledtohavesecuritiesregisteredintheirnames,willnotreceiveorbeentitledtoreceivephysicaldeliveryofacertificateindefinitiveformrepresentingsecuritiesandwillnotbeconsideredtheownersorholdersofthosesecuritiesundertheindenture.Accordingly,eachpersonbeneficiallyowningbook-entrydebtsecuritiesmustrelyontheproceduresofthedepositaryfortherelatedglobaldebtsecurityand,ifsuchpersonisnotaparticipant,ontheproceduresoftheparticipantthroughwhichsuchpersonownsitsinterest,toexerciseanyrightsofaholderundertheindenture.

Weunderstand,however,thatunderexistingindustrypractice,thedepositarywillauthorizethepersonsonwhosebehalfitholdsaglobaldebtsecuritytoexercisecertainrightsofholdersofdebtsecurities,andtheindentureprovidesthatwe,thetrusteeandourrespectiveagentswilltreatasthe

16

Page 90: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

holderofadebtsecuritythepersonsspecifiedinawrittenstatementofthedepositarywithrespecttothatglobaldebtsecurityforpurposesofobtaininganyconsentsordirectionsrequiredtobegivenbyholdersofthedebtsecuritiespursuanttotheindenture.

Wewillmakepaymentsofprincipalof,premium,ifany,andinterest,ifany,onbook-entrydebtsecuritiestothedepositaryoritsnominee,asthecasemaybe,astheregisteredholderoftherelatedglobaldebtsecurity.We,thetrusteeandanyotheragentofoursoragentofthetrusteewillnothaveanyresponsibilityorliabilityforanyaspectoftherecordsrelatingtoorpaymentsmadeonaccountofbeneficialownershipinterestsinaglobaldebtsecurityorformaintaining,supervisingorreviewinganyrecordsrelatingtobeneficialownershipinterests.

Weexpectthatthedepositary,uponreceiptofanypaymentofprincipalof,premium,ifany,orinterest,ifany,onaglobaldebtsecurity,willimmediatelycreditparticipants'accountswithpaymentsinamountsproportionatetotherespectiveamountsofbook-entrydebtsecuritiesheldbyeachparticipantasshownontherecordsofsuchdepositary.Wealsoexpectthatpaymentsbyparticipantstoownersofbeneficialinterestsinbook-entrydebtsecuritiesheldthroughthoseparticipantswillbegovernedbystandingcustomerinstructionsandcustomarypractices,asisnowthecasewiththesecuritiesheldfortheaccountsofcustomersinbearerformorregisteredin"streetname,"andwillbetheresponsibilityofthoseparticipants.

WewillissuecertificateddebtsecuritiesinexchangeforeachglobaldebtsecurityifthedepositaryisatanytimeunwillingorunabletocontinueasdepositaryorceasestobeaclearingagencyregisteredundertheExchangeAct,andasuccessordepositaryregisteredasaclearingagencyundertheExchangeActisnotappointedbyuswithin90days.Inaddition,wemayatanytimeandinoursolediscretiondeterminenottohavethebook-entrydebtsecuritiesofanyseriesrepresentedbyoneormoreglobaldebtsecuritiesand,inthatevent,willissuecertificateddebtsecuritiesinexchangefortheglobaldebtsecuritiesofthatseries.GlobaldebtsecuritieswillalsobeexchangeablebytheholdersforcertificateddebtsecuritiesifanEventofDefaultwithrespecttothebook-entrydebtsecuritiesrepresentedbythoseglobaldebtsecuritieshasoccurredandiscontinuing.Anycertificateddebtsecuritiesissuedinexchangeforaglobaldebtsecuritywillberegisteredinsuchnameornamesasthedepositaryshallinstructthetrustee.Weexpectthatsuchinstructionswillbebasedupondirectionsreceivedbythedepositaryfromparticipantswithrespecttoownershipofbook-entrydebtsecuritiesrelatingtosuchglobaldebtsecurity.

Wehaveobtainedtheforegoinginformationconcerningthedepositaryandthedepositary'sbook-entrysystemfromsourceswebelievetobereliable,butwetakenoresponsibilityfortheaccuracyofthisinformation.

CertificatedDebtSecurities.Youmaytransferorexchangecertificateddebtsecuritiesatanyofficewemaintainforthispurposeinaccordancewiththetermsoftheindenture.Noservicechargewillbemadeforanytransferorexchangeofcertificateddebtsecurities,butwemayrequirepaymentofasumsufficienttocoveranytaxorothergovernmentalchargepayableinconnectionwithatransferorexchange.

Youmayeffectthetransferofcertificateddebtsecuritiesandtherighttoreceivetheprincipalof,premium,ifany,andinterest,ifany,oncertificateddebtsecuritiesonlybysurrenderingthecertificaterepresentingthosecertificateddebtsecuritiesandeitherreissuancebyusorthetrusteeofthecertificatetothenewholderortheissuancebyusorthetrusteeofanewcertificatetothenewholder.

Discharge, Defeasance and Covenant Defeasance

Discharge.Theindentureprovidesthatwemaybedischargedfromanyandallobligationsinrespectofthedebtsecuritiesofanyseries.Wewillbesodischargediftheapplicableseriesofdebtsecuritieseitherhasbecomedueandpayablebyreasonofthemailingofanoticeofredemptionor

17

Page 91: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

otherwiseorwillbecomedueandpayablewithinoneyear,uponthedepositwiththetrustee,intrust,ofmoneyand/orU.S.governmentobligationsor,inthecaseofdebtsecuritiesdenominatedinasinglecurrencyotherthanU.S.dollars,foreigngovernmentobligations,thatwillprovidemoneyinanamountsufficient,withoutconsiderationofanyreinvestmentofinterest,topayanddischargetheentireindebtednessonsuchdebtsecuritiesnotdeliveredtothetrusteeforcancellationforprincipal,premium,ifany,andaccruedinteresttothedateofmaturityorredemption,inaccordancewiththetermsoftheindentureandthosedebtsecurities.

LegalDefeasance.Theindentureprovidesthat,unlessotherwiseprovidedbythetermsoftheapplicableseriesofdebtsecurities,whichwillbedescribedintheapplicableprospectussupplement,wemaybedischargedfromanyandallobligationsinrespectofthedebtsecuritiesofanyseries(exceptforcertainobligationstoregisterthetransferorexchangeofdebtsecuritiesofsuchseries,toreplacestolen,lostormutilateddebtsecuritiesofsuchseries,andtomaintainpayingagenciesandcertainprovisionsrelatingtothetreatmentoffundsheldbypayingagents).Wewillbesodischargeduponthedepositwiththetrustee,intrust,ofmoneyand/orU.S.governmentobligationsor,inthecaseofdebtsecuritiesdenominatedinasinglecurrencyotherthanU.S.dollars,foreigngovernmentobligations,that,throughthepaymentofinterestandprincipalinaccordancewiththeirterms,willprovidemoneyinanamountsufficientintheopinionofanationallyrecognizedinvestmentbank,appraisalfirmorfirmofindependentpublicaccountantstopayanddischargeeachinstallmentofprincipal,premium,ifany,andinterest,ifany,onandanymandatorysinkingfundpaymentsinrespectofthedebtsecuritiesofthatseriesonthestatedmaturityofthosepaymentsinaccordancewiththetermsoftheindentureandthosedebtsecurities.

Thisdefeasancemayoccuronlyif,amongotherthings,wehavedeliveredtothetrusteeanopinionofcounselstatingthatwehavereceivedfrom,ortherehasbeenpublishedby,theUnitedStatesInternalRevenueServicearulingor,sincethedateofexecutionoftheindenture,therehasbeenachangeintheapplicableUnitedStatesfederalincometaxlaw,ineithercasetotheeffectthat,andbasedthereonsuchopinionshallconfirmthat,theholdersandbeneficialownersofthedebtsecuritiesofthatserieswillnotrecognizeincome,gainorlossforUnitedStatesfederalincometaxpurposesasaresultofthedepositanddefeasanceandwillbesubjecttoUnitedStatesfederalincometaxonthesameamountsandinthesamemannerandatthesametimesaswouldhavebeenthecaseifthedepositanddefeasancehadnotoccurred.

DefeasanceofCertainCovenants.Theindentureprovidesthat,unlessotherwiseprovidedbythetermsoftheapplicableseriesofdebtsecurities,whichwillbedescribedintheapplicableprospectussupplement,uponcompliancewithcertainconditions:

• wemayomittocomplywiththecovenantdescribedundertheheading"Consolidation,MergerorSale"andcertainothercovenantssetforthintheindenture,aswellasanyadditionalcovenantswhichmaybesetforthintheapplicableprospectussupplement;and

• anyomissiontocomplywiththosecovenantswillnotconstituteadefaultoranEventofDefaultwithrespecttothedebtsecuritiesofthatseries,orcovenantdefeasance.

Theconditionsinclude:

• depositingwiththetrusteemoneyand/orU.S.governmentobligationsor,inthecaseofdebtsecuritiesdenominatedinasinglecurrencyotherthanU.S.dollars,foreigngovernmentobligations,that,throughthepaymentofinterestandprincipalinaccordancewiththeirterms,willprovidemoneyinanamountsufficientintheopinionofanationallyrecognizedinvestmentbank,appraisalfirmorfirmofindependentpublicaccountantstopayanddischargeeachinstallmentofprincipalof,premium,ifany,andinterest,ifany,on,andanymandatorysinkingfundpaymentsinrespectofthedebtsecuritiesofthatseriesonthestatedmaturityofthosepaymentsinaccordancewiththetermsoftheindentureandthosedebtsecurities;and

18

Page 92: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

• deliveringtothetrusteeanopinionofcounseltotheeffectthattheholdersandbeneficialownersofthedebtsecuritiesofthatserieswillnotrecognizeincome,gainorlossforUnitedStatesfederalincometaxpurposesasaresultofthedepositandrelatedcovenantdefeasanceandwillbesubjecttoUnitedStatesfederalincometaxonthesameamountsandinthesamemannerandatthesametimesaswouldhavebeenthecaseifthedepositandrelatedcovenantdefeasancehadnotoccurred.

CovenantDefeasanceandEventsofDefault.IntheeventweexerciseouroptiontoeffectcovenantdefeasancewithrespecttoanyseriesofdebtsecuritiesandthedebtsecuritiesofthatseriesaredeclareddueandpayablebecauseoftheoccurrenceofanyEventofDefault,theamountofmoneyand/orU.S.governmentobligationsorforeigngovernmentobligationsondepositwiththetrusteewillbesufficienttopayamountsdueonthedebtsecuritiesofthatseriesatthetimeoftheirstatedmaturitybutmaynotbesufficienttopayamountsdueonthedebtsecuritiesofthatseriesatthetimeoftheaccelerationresultingfromtheEventofDefault.However,weshallremainliableforthosepayments.

Modification of the Indenture

Theindentureprovidesthatweandthetrusteemayenterintosupplementalindentureswithouttheconsentoftheholdersofdebtsecuritiesto:

• secureanydebtsecurities(orprovideadditionalcollateral)andprovidethetermsandconditionsforthereleaseorsubstitutionofthesecurity(oradditionalcollateral);

• evidencetheassumptionbyasuccessorpersonofourobligations;

• makeanychangethatwouldprovideanyadditionalrightsorbenefitstotheholdersofthedebtsecuritiesorthatdoesnotadverselyaffecttheholders'rightsthereunderinanymaterialrespectortosurrenderanyrightorpowerconferreduponusundertheindenture;

• provideforadditionofguaranteesforthebenefitofdebtsecuritiesofanyseriesoraddaguarantororanadditionalobligorundertheindenture;

• addanyadditionalEventsofDefault;

• cureanyambiguityorcorrectanyinconsistencyordefectintheindenture;

• addto,changeoreliminateanyoftheprovisionsoftheindentureinamannerthatwillbecomeeffectiveonlywhenthereisnooutstandingdebtsecuritywhichisentitledtothebenefitoftheprovisionastowhichthemodificationwouldapply;

• provideforuncertificatedsecuritiesinadditiontoorinplaceofcertificatedsecurities;

• complywithrequirementsoftheSECinordertoeffectormaintainthequalificationoftheindentureundertheTrustIndentureActof1939,asamended(the"TrustIndentureAct");

• eliminateanyconflictbetweenthetermsoftheindentureandtheTrustIndentureAct;

• providefortheissuanceofandestablishtheformandtermsandconditionsofsecuritiesofanyseriesaspermitted;

• evidenceandprovidefortheacceptanceofappointmentbyasuccessortrusteeandaddtoorchangeanyoftheprovisionsoftheindentureasisnecessaryfortheadministrationofthetrustsbymorethanonetrustee;and

• conformanyprovisionoftheindenture,thesecuritiesofanyseriesoranyrelatedsecuritydocumentstothedescriptionofsuchsecuritiescontainedintheprospectus,theapplicable

19

Page 93: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

prospectussupplement,offeringmemorandumorsimilardocumentwithrespecttotheofferingofthesecuritiesofsuchseries.

• Theindenturealsoprovidesthatweandthetrusteemay,withtheconsentoftheholdersofnotlessthanamajorityinaggregateprincipalamountofdebtsecuritiesofeachseriesthenoutstandingandaffectedaddanyprovisionsto,orchangeinanymanner,eliminateormodifyinanywaytheprovisionsof,theindentureormodifyinanymannertherightsoftheholdersofthedebtsecurities.Weandthetrusteemaynot,however,withouttheconsentoftheholderofeachoutstandingdebtsecurityaffectedthereby:

• reducetheamountofdebtsecuritieswhoseholdersmustconsenttoanamendment,supplementorwaiver;

• reducetherateoforextendthetimeforpaymentofinterest(includingdefaultinterest)onanydebtsecurity;

• reducetheprincipaloforpremium,ifany,onorchangethefixedmaturityofanydebtsecurityorreducetheamountof,orpostponethedatefixedfor,thepaymentofanysinkingfundoranalogousobligationwithrespecttoanyseriesofdebtsecurities;

• reducetheprincipalamountofdiscountsecuritiespayableuponaccelerationofmaturity;

• waiveadefaultinthepaymentoftheprincipalof,premium,ifany,orinterest,ifany,onanydebtsecurity(exceptarescissionofaccelerationofthedebtsecuritiesofanyseriesbytheholdersofatleastamajorityinaggregateprincipalamountofthethenoutstandingdebtsecuritiesofthatseriesandawaiverofthepaymentdefaultthatresultedfromsuchacceleration);

• maketheprincipaloforpremium,ifany,orinterest,ifany,onanydebtsecuritypayableincurrencyotherthanthatstatedinthedebtsecurity;

• makeanychangetocertainprovisionsoftheindenturerelatingto,amongotherthings,therightofholdersofdebtsecuritiestoreceivepaymentoftheprincipalof,premium,ifany,andinterest,ifany,onthosedebtsecuritiesandtoinstitutesuitfortheenforcementofanysuchpaymentandtowaiversoramendments;or

• waivearedemptionpaymentwithrespecttoanydebtsecurityorchangeanyoftheprovisionswithrespecttotheredemptionofanydebtsecurities.

Exceptforcertainspecifiedprovisions,theholdersofatleastamajorityinprincipalamountoftheoutstandingdebtsecuritiesofanyseriesmayonbehalfoftheholdersofalldebtsecuritiesofthatserieswaiveourcompliancewithprovisionsoftheindenture.Theholdersofamajorityinprincipalamountoftheoutstandingdebtsecuritiesofanyseriesmayonbehalfoftheholdersofallthedebtsecuritiesofsuchserieswaiveanypastdefaultundertheindenturewithrespecttothatseriesanditsconsequences,exceptadefaultinthepaymentoftheprincipalof,premium,ifany,oranyinterest,ifany,onanydebtsecurityofthatseries;provided,however,thattheholdersofamajorityinprincipalamountoftheoutstandingdebtsecuritiesofanyseriesmayrescindanaccelerationanditsconsequences,includinganyrelatedpaymentdefaultthatresultedfromtheacceleration.

No Individual Liability of Incorporators, Stockholders, Officers or Directors

Theindentureprovidesthatnoincorporatorandnopast,presentorfuturestockholder,officerordirectorofoursoranysuccessorcorporationintheircapacityassuchshallhaveanyindividualliabilityforanyofourobligations,covenantsoragreementsunderthedebtsecuritiesortheindenture.

20

Page 94: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Governing Law

Theindentureandthedebtsecuritieswillbegovernedby,andconstruedinaccordancewith,thelawsoftheStateofNewYork.

Concerning our Relationship with the Trustee

Fromtimetotime,weandoursubsidiariesmaymaintainordinarybankingandcreditrelationshipswithU.S.BankNationalAssociationanditsaffiliates.

21

Page 95: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

DESCRIPTION OF CAPITAL STOCK

Ouramendedandrestatedcertificateofincorporationauthorizesustoissue8,000,000,000sharesofcommonstock,parvalue$0.01pershare,and265,000,000sharesofpreferredstock,parvalue$0.01pershare.Oftheauthorizedpreferredshares,2,000,000aredesignatedasSeriesDJuniorParticipatingPreferredStock,parvalue$0.01pershare("SeriesDPreferredStock").See"—PreferredStock"and"—ThirdAmendedRightsAgreement"below.

Thefollowingdescriptionofourcapitalstockisasummary.Youshouldkeepinmind,however,thatitisouramendedandrestatedcertificateofincorporation,includinganycertificatesofdesignationsthatareapartofouramendedandrestatedcertificateofincorporation,andouramendedandrestatedby-lawsandDelawarelaw,andnotthissummary,whichdefineyourrightsasasecurityholder.Theremaybeotherprovisionsinthesedocumentsthatarealsoimportanttoyou.Youshouldreadthesedocumentsforafulldescriptionofthetermsofourcapitalstock.

Common Stock

OurcommonstockislistedontheNYSEunderthesymbol"CNO."AmericanStockTransferandTrustCompany,LLCisthetransferagentandregistrarforourcommonstock.Alloutstandingsharesofcommonstockarefullypaidandnon-assessable.

InaccordancewithourThirdAmendedRightsAgreement(definedbelow),eachofouroutstandingsharesofcommonstockhasassociatedwithittherighttopurchaseaoneone-thousandthofashareofourSeriesDPreferredStockandeachshareofcommonstockthatweissuepriortotheearlierof(i)thedatethepreferredsharepurchaserightsbecomeexercisableand(ii)theexpirationdateoftheThirdAmendedRightsAgreement,willbeissuedwithanassociatedpreferredsharepurchaseright.See"—ThirdAmendedRightsAgreement"below.

Dividends.ExceptasotherwiseprovidedbyDelawarelaworouramendedandrestatedcertificateofincorporation,andsubjecttoallrightsandpreferencesofholdersofanyoutstandingsharesofpreferredstock,holdersofcommonstockshareratablyinalldividendsanddistributions,whetheruponliquidationordissolutionorotherwise.

Voting.ExceptasotherwiseprovidedbyDelawarelaworouramendedandrestatedcertificateofincorporationandsubjecttotherightsofholdersofanyoutstandingsharesofpreferredstock,allofthevotingpowerofourstockholdersisvestedintheholdersofourcommonstock,andeachholderofcommonstockhasonevoteforeachshareheldbysuchholderonallmattersvoteduponbyourstockholders.

Notwithstandingthevotingrightsgrantedtoholdersofcommonstockandpreferredstockinouramendedandrestatedcertificateofincorporationorinanycertificateofdesignationsrelatingtoanypreferredstock,thevotingrightsofanystockheldbyanyholderasofSeptember10,2003,theeffectivedateofourpredecessorcompany'splanofreorganization,areautomaticallyreducedwithrespecttoanyparticularstockholdervoteoractionbywrittenconsenttotheextent,ifany,requiredtoavoidapresumptionofcontrolarisingfromthebeneficialownershipofvotingsecuritiesundertheinsurancestatutesorregulationsapplicabletoanyofourdirectorindirectinsurancecompanysubsidiaries,providedthatnosuchreductionreducessuchvotingrights,withoutsuchholder'swrittenconsent:

• bymorethantheminimumamountrequiredtoreducesuchvotingrightstolessthan10%oftheaggregatevotingrightsofallstockentitledtovoteorconsentwithrespecttosuchvoteoraction,or

• totheextentthatsuchholder'sacquisitionofcontrolordeemedacquisitionofcontrolofourdirectandindirectinsurancecompanysubsidiarieshasbeenapprovedunder,orisexemptfrom

22

Page 96: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

theapprovalrequirementsof,allinsurancestatutesandregulationsapplicabletoourdirectandindirectinsurancecompanysubsidiaries.

BoardofDirectors.Exceptasotherwiseprovidedinouramendedandrestatedcertificateofincorporationoranydulyauthorizedcertificateofdesignationsofanyseriesofpreferredstock,directorsareelectedinaccordancewiththeproceduresandrequirementsprescribedbyouramendedandrestatedby-laws.Ouramendedandrestatedby-lawsprovidethat,exceptinthecaseofvacanciesandnewlycreateddirectorshipsresultingfromanyincreaseinthetotalnumberofdirectors,eachdirectorshallbeelectedbythevoteofthemajorityofthevotescast(wherethenumberofvotescast"for"adirectorexceedsthenumberofvotescast"against"thatdirector)withrespecttothedirectorsatanymeetingfortheelectionofdirectorsatwhichaquorumispresent,providedthat,ifthenumberofnomineesexceedsthenumberofdirectorstobeelected,thedirectorsshallbeelectedbyapluralityofthesharesrepresentedinpersonorbyproxyatanysuchmeetingandentitledtovoteontheelectionofdirectors.

Other.Ourcommonstockisnotconvertibleinto,orexchangeablefor,anyotherclassorseriesofourcapitalstock.ExceptascontemplatedbyourThirdAmendedRightsAgreement,holdersofcommonstockhavenopreemptiveorotherrightstosubscribefororpurchaseadditionalsecuritiesofours.Sharesofourcommonstockarenotsubjecttocallsorassessments.

Preferred Stock

Eachofouroutstandingsharesofcommonstockhasassociatedwithittherighttopurchaseaoneone-thousandthofashareofourSeriesDPreferredStockandeachshareofcommonstockthatweissuepriortotheearlierofthedatesuchpreferredsharepurchaserightsbecomeexercisableandtheexpirationdateoftheThirdAmendedRightsAgreementwillbeissuedwithanassociatedpreferredsharepurchaseright.See"—ThirdAmendedRightsAgreement"below.

Third Amended Rights Agreement

OnOctober3,2017CNOenteredintoaThirdAmendedandRestatedSection382RightsAgreement,datedasofOctober3,2017(asamended,the"ThirdAmendedRightsAgreement")withAmericanStockTransfer&TrustCompany,LLC,asrightsagent(the"RightsAgent"),whichbecameeffectiveonNovember13,2017.Ourboardofdirectorshadpreviouslydeclaredadividendofonepreferredsharepurchaseright(a"Right")foreachoutstandingshareofcommonstockthatwaspaidtothestockholdersofrecordasofthecloseofbusinessonJanuary30,2009pursuanttothatcertainSection382RightsAgreement,datedasofJanuary20,2009(the"OriginalRightsAgreement"),whichwasamendedandrestatedbythatcertainAmendedandRestatedSection382RightsAgreement,datedDecember6,2011(the"FirstAmendedRightsAgreement"),asfurtheramendedbytheSecondAmendedandRestatedSection382RightsAgreement,datedNovember13,2014(the"SecondAmendedRightsAgreement"),eachbetweentheCompanyandtheRightsAgent.ThefollowingsummaryoftheThirdAmendedRightsAgreementandtheRightsisnotcomplete.YoushouldreadtheThirdAmendedRightsAgreement,whichisanExhibittoourCurrentReportonForm8-KfiledonOctober4,2017forafulldescriptionofitsterms.

TheThirdAmendedRightsAgreementisintendedtohelpprotecttheCompany'staxnetoperatinglosscarryforwards("NOLs").OurboardofdirectorsmayredeemtheRights,asdiscussedmorefullybelow.TheThirdAmendedRightsAgreementisintendedtoactasadeterrenttoanyperson(otherthananExemptedPerson(asdefinedbelow)oranypersonwhohasthestatusofaThresholdHolder(asdefinedbelow)onthedateoftheThirdAmendedRightsAgreementsolongassuchpersondoesnotincreaseitsownershipaboveanadditional1%ofCompany382Securities(asdefinedbelow)thenoutstanding)frombecomingorobtainingtherighttobecome,apersonwhoorwhich,togetherwithallaffiliatesandassociatesofsuchperson,isthebeneficialownerof4.99%or

23

Page 97: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

moreofthesharesofourcommonstockoranyotherclassofCompany382Securitiesthenoutstanding(eachsuchperson,a"ThresholdHolder"),withouttheapprovalofourboardofdirectors.

TheRights.PursuanttotheThirdAmendedRightsAgreement,eachRightentitlestheregisteredholdertopurchasefromtheCompanyoneone-thousandthofashareofSeriesDPreferredStockoftheCompanyatapriceof$90.00peroneone-thousandthofashareofSeriesDPreferredStock(asthesamemaybeadjusted,the"PurchasePrice").ThedescriptionandtermsoftheRightsareassetforthintheThirdAmendedRightsAgreement.

Untilthecloseofbusinessontheearlierof(i)thetenthbusinessdayafterthefirstdateofapublicannouncementthataperson(otherthananExemptedPersonorGrandfatheredPerson(asdefinedbelow))orgroupofaffiliatedorassociatedpersons(an"AcquiringPerson")hasbecomeaThresholdHolderor(ii)thetenthbusinessday(orsuchlaterdateasmaybedeterminedbyactionofourboardofdirectorspriortosuchtimeasanypersonorgroupofaffiliatedpersonsbecomesanAcquiringPerson)afterthedateofcommencementof,orthefirstpublicannouncementofanintentiontocommence,atenderofferorexchangeoffer,theconsummationofwhichwouldresultinanyperson(otherthananExemptedPerson)becominganAcquiringPerson(theearlierofsuchdatesbeinghereinreferredtoasthe"DistributionDate"),theRightswillbeevidencedbythesharesofourcommonstockrepresentedbythecertificatesforourcommonstockoruncertificatedbookentrysharesoutstandingasoftherecorddate,togetherwithacopyofthesummaryofrightsdisseminatedinconnectionwiththeoriginaldividendofRights.

TheThirdAmendedRightsAgreementprovidesthat,untiltheDistributionDate(orearlierexpirationoftheRights),newcommonstockcertificatesissuedaftertherecorddatewillcontainanotationincorporatingtheThirdAmendedRightsAgreementbyreferenceand,withrespecttoanyuncertificatedbookentrysharesissuedaftertherecorddate,propernoticewillbeprovidedthatincorporatestheThirdAmendedRightsAgreementbyreference.UntiltheDistributionDate(orearlierredemptionorexpirationoftheRights),theRightswillbetransferableonlyinconnectionwiththetransferofsharesofourcommonstock.UntiltheDistributionDate(orearlierredemptionorexpirationoftheRights),thesurrenderfortransferofanycertificatesforsharesofourcommonstock(oruncertificatedbookentryshares)outstandingasoftherecorddate,evenwithoutanotationincorporatingtheThirdAmendedRightsAgreementbyreference(orsuchnotice,inthecaseofuncertificatedbookentryshares)oracopyofthesummaryofrightsincludedinconnectionwiththeThirdAmendedRightsAgreement,willalsoconstitutethetransferoftheRightsassociatedwiththesharesofourcommonstockrepresentedbysuchcertificateoruncertificatedbookentryshares,asthecasemaybe.AssoonaspracticablefollowingtheDistributionDate,separatecertificatesevidencingtheRights("RightCertificates")willbemailedtoholdersofrecordoftheourcommonstockasofthecloseofbusinessontheDistributionDateandsuchseparateRightCertificatesalonewillevidencetheRights.

CertainDefinitions

"ApprovedAcquisition"shallmean(i)anyacquisitionofCompany382SecuritiesthatwouldcauseapersontoqualifyasaThresholdHolderandthatisapprovedinadvancebyourboardofdirectors,or(ii)aconversion(orotherexchange)ofCompany382SecuritiesforotherCompany382Securitieswheresuchconversion(orotherexchange)doesnotincreasethebeneficialownershipintheCompanybyanypersonforpurposesofSection382(definedbelow).

"Company382Securities"shallmeanourcommonstockandanyotherinterestthatwouldbetreatedas"stock"oftheCompanyforpurposesofSection382oftheInternalRevenueCodeof1986,asamended(includingpursuanttoTreasuryRegulationSection1.382-2T(f)(18))("Section382").

"ExemptedPerson"shallmean(i)theCompany,(ii)anysubsidiaryoftheCompany,(inthecaseofsubclauses(i)and(ii)including,withoutlimitation,initsfiduciarycapacity),(iii)anyemployee

24

Page 98: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

benefitplanorcompensationarrangementoftheCompanyorofanysubsidiaryoftheCompany,(iv)anyentityortrusteeholding(oractinginafiduciarycapacityinrespectof)Company382Securitiestotheextentorganized,appointedorestablishedbytheCompanyoranysubsidiaryoftheCompanyfororpursuanttothetermsofanysuchplanorforthepurposeoffundinganysuchemployeebenefitplanorcompensationarrangement,(v)anyperson(togetherwithitsaffiliatesandassociates)whosestatusasaThresholdHolderwill,inthesolejudgmentofourboardofdirectors,notjeopardizeorendangertheavailabilitytotheCompanyofitsNOLstobeusedtooffsetitstaxableincomeinsuchyearorfutureyears(butinthecaseofanypersondeterminedbyourboardofdirectorstobeanExemptedPersonpursuanttothissubparagraph(v)onlyforsolongassuchperson'sstatusasaThresholdHoldercontinuesnottojeopardizeorendangertheavailabilityofsuchNOLs,asdeterminedbyourboardofdirectorsinitsgoodfaithdiscretion)or(vi)anypersonwhoorwhichwouldqualifyasaThresholdHolderasaresultofanApprovedAcquisitionand,totheextentapprovedbyourboardofdirectors,anypersonwhoorwhichacquiresCompany382Securitiesfromanysuchperson.

"GrandfatheredPerson"shallmeananypersonwhoorwhich,togetherwithallaffiliatesandassociatesofsuchperson,wasasonNovember13,2017,thebeneficialownerof4.99%ormoreoftheCompany382Securitiesoutstandingonsuchdate,unlessanduntilsuchtimeassuchpersonafterthedateoftheThirdAmendedRightsAgreementacquiresbeneficialownershipofadditionalsharesorotherinterestsinCompany382Securitiesrepresentingmorethan1%oftheCompany382Securitiesthenoutstanding.AnyGrandfatheredPersonwho,togetherwithallofitsaffiliatesandassociates,subsequentlybecomesthebeneficialowneroflessthan4.99%oftheCompany382SecuritiesshallceasetobeaGrandfatheredPerson.

Exercisability.TheRightswillnotbeexercisableuntiltheDistributionDate.

Transfer.AnytransferofsharesofourcommonstockpriortotheDistributionDatewillconstituteatransferoftheassociatedRights.AftertheDistributionDate,theRightsmaybetransferredotherthaninconnectionwiththetransferoftheunderlyingsharesofourcommonstock.

Expiration.TheRightsarenotexercisableuntiltheDistributionDateandwillexpireattheearlierof(i)thecloseofbusinessonNovember13,2020,(ii)therepealofSection382oranysuccessorstatuteifourboardofdirectorsdeterminesthattheThirdAmendedRightsAgreementisnolongernecessaryforthepreservationoftaxbenefitsor(iii)thebeginningofataxableyearoftheCompanytowhichourboardofdirectorsdeterminesthatnotaxbenefitsmaybecarriedforward(the"FinalExpirationDate"),subjectto(x)theextensionoftheThirdAmendedRightsAgreementbyourboardofdirectorsbytheamendmentoftheThirdAmendedRightsAgreementor(y)theredemptionorexchangeoftheRightsbytheCompany,asdescribedbelow.

Adjustments.ThePurchasePricepayable,andthenumberofsharesofSeriesDPreferredStockorothersecuritiesorpropertyissuable,uponexerciseoftheRightsaresubjecttoadjustmentfromtimetotimetopreventdilution(i)intheeventofastockdividendon,orasubdivision,combinationorreclassificationof,theSeriesDPreferredStock,(ii)uponthegranttoholdersoftheSeriesDPreferredStockofcertainrightsorwarrantstosubscribefororpurchaseSeriesDPreferredStockataprice,orsecuritiesconvertibleintoSeriesDPreferredStockwithaconversionprice,lessthanthethencurrentmarketpriceoftheSeriesDPreferredStockor(iii)uponthedistributiontoholdersoftheSeriesDPreferredStockofevidencesofindebtednessorassets(excludingregularperiodiccashdividendsordividendspayableinSeriesDPreferredStock)orofsubscriptionrightsorwarrants(otherthanthosereferredtoabove).

TheRightsarealsosubjecttoadjustmentintheeventofastockdividendonourcommonstockpayableinsharesofourcommonstockorsubdivisions,consolidationsorcombinationsofourcommonstockoccurring,inanysuchcase,priortotheDistributionDate.

25

Page 99: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

JuniorParticipatingPreferredStock.SharesofSeriesDPreferredStockpurchasableuponexerciseoftheRightswillnotberedeemable.EachshareofSeriesDPreferredStockwillbeentitled,when,asandifdeclared,toaminimumpreferentialquarterlydividendpaymentofthegreaterof(a)$1pershareand(b)anamountequalto1,000timesthedividenddeclaredpershareofourcommonstock.Intheeventofliquidation,dissolutionorwindingupoftheCompany,theholdersoftheSeriesDPreferredStockwillbeentitledtoaminimumpreferentialliquidationpaymentof$1,000pershare(plusanyaccruedbutunpaiddividends)butwillbeentitledtoanaggregate1,000timesthepaymentmadepershareofourcommonstock.EachshareofSeriesDPreferredStockwillhave1,000votes,votingtogetherwithourcommonstock.Finally,intheeventofanymerger,consolidationorothertransactioninwhichsharesofourcommonstockareconvertedorexchanged,eachshareofSeriesDPreferredStockwillbeentitledtoreceive1,000timestheamountreceivedpershareofourcommonstock.Theserightsareprotectedbycustomaryantidilutionprovisions.

IntheeventthatthequarterlydividendsorcertainotherdividendsordistributionspayableontheSeriesDPreferredStockareinarrears,untilsuchaccruedandunpaiddividendsordistributionsarepaid,thecompanymaynotredeem,purchaseordeclareandpaydividendsonourcommonstockorpreferredstockonparitywiththeSeriesDPreferredStock.

BecauseofthenatureoftheSeriesDPreferredStock'sdividend,liquidationandvotingrights,thevalueoftheoneone-thousandthinterestinashareofSeriesDPreferredStockpurchasableuponexerciseofeachRightshouldapproximatethevalueofoneshareofourcommonstock.

EffectsofTriggeringEvents.IntheeventthatanypersonorgroupofaffiliatedorassociatedpersonsbecomesanAcquiringPerson,eachholderofaRight,otherthanRightsbeneficiallyownedbytheAcquiringPerson(whichwillthereuponbecomevoid),willthereafterhavetherighttoreceiveuponexerciseofaRightandpaymentofthePurchasePrice,thatnumberofsharesofourcommonstockand/orothersecuritiesorpropertyhavingamarketvalueoftwotimesthePurchasePrice.

Intheeventthat,afterapersonorgrouphasbecomeanAcquiringPerson,theCompanyisacquiredinamergerorotherbusinesscombinationtransactionor50%ormoreofitsconsolidatedassetsorearningpoweraresold,properprovisionwillbemadesothateachholderofaRight(otherthanRightsbeneficiallyownedbyanAcquiringPersonwhichwillhavebecomevoid)willthereafterhavetherighttoreceive,upontheexercisethereofatthethen-currentexercisepriceoftheRight,thatnumberofsharesofcommonstockofthepersonwithwhomtheCompanyhasengagedintheforegoingtransaction(oritsparent),whichnumberofsharesatthetimeofsuchtransactionwillhaveamarketvalueoftwotimesthePurchasePrice.

AtanytimeafteranypersonorgroupbecomesanAcquiringPersonandpriortotheacquisitionbysuchpersonorgroupof50%ormoreoftheoutstandingsharesofourcommonstockortheoccurrenceofaneventdescribedinthepriorparagraph,ourboardofdirectorsmayexchangetheRights(otherthanRightsownedbysuchpersonorgroupwhichwillhavebecomevoid),inwholeorinpart,atanexchangeratioofoneshareofourcommonstock,orafractionalshareofSeriesDPreferredStock(orofashareofasimilarclassorseriesoftheCompany'spreferredstockhavingsimilarrights,preferencesandprivileges)ofequivalentvalue,perRight(subjecttoadjustment).

Withcertainexceptions,noadjustmentinthePurchasePricewillberequireduntilcumulativeadjustmentsrequireanadjustmentofatleast1%insuchPurchasePrice.NofractionalsharesofSeriesDPreferredStockorourcommonstockwillbeissued(otherthanfractionsofSeriesDPreferredStockwhichareintegralmultiplesofoneone-thousandthofashareofSeriesDPreferredStock,whichmay,attheelectionoftheCompany,beevidencedbydepositaryreceipts)andinlieuthereof,anadjustmentincashwillbemadebasedonthemarketpriceoftheSeriesDPreferredStockorourcommonstockonthelasttradingdaypriortothedateofexercise.

26

Page 100: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

Redemption.AtanytimepriortothetimeanAcquiringPersonbecomessuch,ourboardofdirectorsmayredeemtheRightsinwhole,butnotinpart,atapriceof$0.01perRight,appropriatelyadjustedtoreflectanystocksplit,stockdividendorsimilartransactionoccurringafterthedateofadoptionoftheThirdAmendedRightsAgreement(the"RedemptionPrice")payable,attheoptionoftheCompany,incash,sharesofourcommonstockorsuchotherformofconsiderationasourboardofdirectorsshalldetermine.TheredemptionoftheRightsmaybemadeeffectiveatsuchtime,onsuchbasisandwithsuchconditionsasourboardofdirectorsinitssolediscretionmayestablish.ImmediatelyuponanyredemptionoftheRights,therighttoexercisetheRightswillterminateandtheonlyrightoftheholdersofRightswillbetoreceivetheRedemptionPrice.

Amendments.ForsolongastheRightsarethenredeemable,theCompanymay,exceptwithrespecttotheRedemptionPrice,amendtheThirdAmendedRightsAgreementinanymanner.AftertheRightsarenolongerredeemable,theCompanymay,exceptwithrespecttotheRedemptionPrice,amendtheThirdAmendedRightsAgreementinanymannerthatdoesnotadverselyaffecttheinterestsofholdersoftheRights.

UntilaRightisexercisedorexchanged,theholderthereof,assuch,willhavenorightsasastockholderoftheCompany,including,withoutlimitation,therighttovoteortoreceivedividends.

NOL Protective Amendment to our Certificate of Incorporation

OnMay4,2016ourstockholdersapprovedanamendmenttoouramendedandrestatedcertificateofincorporation(the"NOLProtectiveAmendment").TheNOLProtectiveAmendmentseekstopreservethevalueofourNOLsbyrestrictinganydirectorindirecttransferiftheeffectwouldbeto:

• increasethedirectorindirectownershipofourstockbyanyperson(orpublicgroup)fromlessthan4.99%to4.99%ormoreofourcommonstock;or

• increasethepercentageofourcommonstockowneddirectlyorindirectlybyaperson(orpublicgroup)owningordeemedtoown4.99%ormoreofourcommonstock.

Transfersincludedunderthetransferrestrictionsincludesalestopersonswhoseresultingpercentageownership(directorindirect)ofcommonstockwouldexceedthe4.99%thresholdsdiscussedabove,ortopersonswhosedirectorindirectownershipofcommonstockwouldbyattributioncauseanotherpersontoexceedsuchthreshold.Thetransferrestrictionsincludetherighttorequireaproposedtransferee,asaconditiontoregistrationofatransferofcommonstock,toprovideallinformationreasonablyrequestedregardingsuchperson'sdirectandindirectownershipofourcommonstock.Thetransferrestrictionsmayresultinthedelayorrefusalofcertainrequestedtransfersofourcommonstock.Asaresultoftheserules,thetransferrestrictionscouldresultinprohibitingownership(thusrequiringdispositions)ofourcommonstockasaresultofachangeintherelationshipbetweentwoormorepersonsorentities,orofatransferofaninterestinanentityotherthanus,suchasaninterestinanentitythat,directlyorindirectly,ownsourcommonstock.Thetransferrestrictionswillalsoapplytoproscribethecreationortransferofcertain"options"(whicharebroadlydefinedbySection382)inrespectofourcommonstocktotheextentthat,incertaincircumstances,creation,transferorexerciseoftheoptionwouldresultinaproscribedlevelofownership.

Totheextentpermittedbylaw,anyshareholderwhoknowinglyviolatesthetransferrestrictionswillbeliableforanyandalldamagessufferedbyusasaresultofsuchviolation,includingdamagesresultingfromareductioninoreliminationoftheabilitytoutilizetheNOLsandanyprofessionalfeesincurredinconnectionwithaddressingsuchviolation.

Ourboardofdirectorsmayestablish,modify,amendorrescindby-laws,regulationsandproceduresofCNOforpurposesofdeterminingwhetheranytransferofcommonstockwouldjeopardizeourabilitytopreserveandusetheNOLs.

27

Page 101: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

TheNOLProtectiveAmendmentwillexpireontheearlierof(i)July31,2019,(ii)ourboardofdirectors'determinationthattheNOLProtectiveAmendmentisnolongernecessaryforthepreservationoftheNOLsbecauseoftherepealofSection382oranysuccessorstatuteor(iii)thebeginningofataxableyeartowhichourboardofdirectorsdeterminesthatnoNOLsmaybecarriedforward.Theboardofdirectorsisalsopermittedtoacceleratetheexpirationdateofthetransferrestrictionsintheeventofachangeinthelawifitdeterminesinwritingthatthecontinuationofthetransferrestrictionsisnolongerreasonablynecessaryforthepreservationoftaxbenefits.

Additional Anti-Takeover Provisions of our Amended and Restated Certificate of Incorporation and Amended and Restated By-laws

InadditiontosharesofSeriesDPreferredStockauthorizedinconnectionwithourThirdAmendedRightsAgreementandourNOLProtectiveAmendmenttoouramendedandrestatedcertificateofincorporation,ouramendedandrestatedcertificateofincorporationandamendedandrestatedby-lawscontaincertainprovisionsthatareintendedtoenhancethelikelihoodofcontinuityandstabilityinthecompositionofourboardofdirectorsandwhichmayhavetheeffectofdelaying,deferringorpreventingourfuturetakeoverorchangeofcontrolunlessthetakeoverorchangeofcontrolisapprovedbyourboardofdirectors.Theseprovisionsmayalsorendertheremovalofthecurrentboardofdirectorsandofmanagementmoredifficult.Theseprovisionsinclude:

• advancenoticerequirementsforstockholderproposalsandnominations;and

• theauthorityofourboardofdirectorstoissue,withoutstockholderapproval,certainseriesofpreferredstockwithsuchtermsastheboardofdirectorsmaydetermine.

Anti-Takeover Effects of Certain Insurance Laws

Theinsurancelawsandregulationsofthejurisdictionsinwhichweorourinsurancesubsidiariesdobusinessmayimpedeordelayabusinesscombinationinvolvingus.Stateinsuranceholdingcompanylawsandregulationsapplicabletousgenerallyprovidethatnopersonmayacquirecontrolofacompany,andthusindirectcontrolofitsinsurancesubsidiaries,unlessthepersonhasprovidedrequiredinformationto,andtheacquisitionisapprovedornotdisapprovedby,theappropriateinsuranceregulatoryauthorities.Generally,anypersonacquiringbeneficialownershipof10%ormoreofthevotingpowerofourcapitalstockwouldbepresumedtohaveacquiredcontrol,unlesstheappropriateinsuranceregulatoryauthoritiesuponadvanceapplicationdetermineotherwise.

28

Page 102: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

DESCRIPTION OF DEPOSITARY SHARES

Thefollowingdescriptionofthedepositarysharesandthetermsofthedepositagreementisasummary.Itsummarizesonlythoseaspectsofthedepositarysharesandthoseportionsofthedepositagreementthatwebelievewillbemostimportanttoyourdecisiontoinvestinourdepositaryshares.Youshouldkeepinmind,however,thatitisthedepositagreement,andnotthissummary,whichdefinesyourrightsasaholderofdepositaryshares.Theremaybeotherprovisionsinthedepositagreementthatarealsoimportanttoyou.Youshouldreadthedepositagreementforafulldescriptionofthetermsofthedepositaryshares.

Theparticulartermsofthedepositarysharesofferedbyanyprospectussupplementandtheextenttowhichthegeneralprovisionsdescribedbelowmayapplytosuchdepositaryshareswillbeoutlinedintheapplicableprospectussupplement.

General

Wemaychoosetoofferfromtimetotimefractionalinterestsinourdebtsecuritiesandsharesofourcommonstockorpreferredstock.Ifwedoso,wewillissuefractionalinterestsinourdebtsecurities,commonstockorpreferredstock,asthecasemaybe,intheformofdepositaryshares.Eachdepositarysharewouldrepresentafractionalinterestinasecurityofaparticularseriesofdebtsecurities,afractionofashareofcommonstock,afractionofashareofaparticularseriesofpreferredstock,asthecasemaybe,andwouldbeevidencedbyadepositaryreceipt.

Wewilldepositthedebtsecurities,andsharesofcommonstockandpreferredstockrepresentedbydepositarysharesunderadepositagreementbetweenusandadepositary,whichwewillnameintheapplicableprospectussupplement.Subjecttothetermsofthedepositagreement,asanownerofadepositaryshareyouwillbeentitled,inproportiontotheapplicablefractionofadebtsecurityorshareofcommonstockorpreferredstockrepresentedbythedepositaryshare,toalltherightsandpreferencesofthedebtsecurity,commonstockorpreferredstock,asthecasemaybe,representedbythedepositaryshare,including,asthecasemaybe,interest,dividend,voting,conversion,redemption,sinkingfund,repaymentatmaturity,subscriptionandliquidationrights.

Interest, Dividends and Other Distributions

Thedepositarywilldistributeallpaymentsofinterest,cashdividendsorothercashdistributionsreceivedinrespectofthedebtsecurities,commonstockorpreferredstock,asthecasemaybe,inproportiontothenumbersofthedepositarysharesownedbytheapplicableholdersontherelevantrecorddate.Thedepositarywilldistributeonlyanamount,however,thatcanbedistributedwithoutattributingtoanyholderofdepositarysharesafractionofonecent,andanybalancenotsodistributedwillbeaddedtoandtreatedaspartofthenextsumreceivedbythedepositaryfordistributiontorecordholdersofdepositaryshares.

Ifthereisanon-cashdistribution,thedepositarywilldistributepropertyreceivedbyittotherecordholdersofdepositarysharesentitledtoit,unlessthedepositarydeterminesthatitisnotfeasibletomakethedistribution.Ifthishappens,thedepositarymay,withourapproval,sellthepropertyanddistributethenetsaleproceedstotheholders.Thedepositagreementwillalsocontainprovisionsrelatingtothemannerinwhichanysubscriptionorsimilarrightsthatweoffertoholdersofthepreferredstockwillbemadeavailabletotheholdersofdepositaryshares.

Redemption of Depositary Shares

Ifweredeemadebtsecurity,commonstockoraseriesofpreferredstockrepresentedbydepositaryshares,thedepositaryshareswillberedeemedfromtheredemptionproceedsreceivedbythedepositary.Thedepositarywillmailnoticeofredemptionnotlessthan15,andnotmorethan60,

29

Page 103: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

daysbeforethedatefixedforredemptiontotherecordholdersofthedepositarysharestoberedeemedattheiraddressesappearinginthedepositary'sbooks.Theredemptionpriceforeachdepositarysharewillbeequaltotheapplicablefractionoftheredemptionpriceforeachdebtsecurityorshareofcommonstockorpreferredstock,asthecasemaybe,payableinrelationtotheredeemedseriesofdebtsecurities,commonstockorpreferredstock.Wheneverweredeemdebtsecuritiesorsharesofcommonstockorpreferredstockheldbythedepositary,thedepositarywillredeemasofthesameredemptiondatethenumberofdepositarysharesrepresenting,asthecasemaybe,fractionalinterestsinthedebtsecuritiesorsharesofcommonstockorpreferredstockredeemed.Iffewerthanallthedepositarysharesaretoberedeemed,thedepositarysharestoberedeemedwillbeselectedbylot,proportionatelyorbyanyotherequitablemethodasthedepositarymaydetermine.

Afterthedatefixedforredemption,thedepositarysharescalledforredemptionwillnolongerbeconsideredoutstandingandallrightsoftheholdersofthedepositaryshareswillcease,excepttherighttoreceivethecash,securitiesorotherpropertypayableupontheredemptionandanycash,securitiesorotherpropertytowhichtheholdersoftheredeemeddepositaryshareswereentitleduponsurrendertothedepositaryofthedepositaryreceiptsevidencingthedepositaryshares.

Theamountdistributedinanyoftheforegoingcaseswillbereducedbyanyamountrequiredtobewithheldbyusorthedepositaryonaccountofanytaxes.

Exercise of Rights under the Indentures or Voting the Common Stock or Preferred Stock

Uponreceiptofnoticeofanymeetingatwhichyouareentitledtovote,orofanyrequestforinstructionsordirectionsfromyouasholderoffractionalinterestsindebtsecurities,commonstockorpreferredstock,thedepositarywillmailtoyoutheinformationcontainedinthatnotice.Eachrecordholderofthedepositarysharesontherecorddatewillbeentitledtoinstructthedepositaryhowtogiveinstructionsordirectionswithrespecttothedebtsecuritiesrepresentedbythatholder'sdepositarysharesorhowtovotetheamountofthecommonstockorpreferredstockrepresentedbythatholder'sdepositaryshares.Therecorddateforthedepositaryshareswillbethesamedateastherecorddateforthedebtsecurities,commonstockorpreferredstock,asthecasemaybe.Thedepositarywillendeavor,totheextentpracticable,togiveinstructionsordirectionswithrespecttothedebtsecuritiesortovotetheamountofthecommonstockorpreferredstock,asthecasemaybe,representedbythedepositarysharesinaccordancewiththoseinstructions.Wewillagreetotakeallreasonableactionwhichthedepositarymaydeemnecessarytoenablethedepositarytodoso.Thedepositarywillabstainfromgivinginstructionsordirectionswithrespecttoyourfractionalinterestsinthedebtsecuritiesorvotingsharesofthecommonstockorpreferredstock,asthecasemaybe,ifitdoesnotreceivespecificinstructionsfromyou.

Amendment and Termination of the Deposit Agreement

Wemayenterintoanagreementwiththedepositaryatanytimetoamendtheformofdepositaryreceiptevidencingthedepositarysharesandanyprovisionofthedepositagreement.However,theholdersofamajorityofthedepositarysharesmustapproveanyamendmentwhichmateriallyandadverselyalterstherightsoftheexistingholdersofdepositaryshares.Weorthedepositarymayterminatethedepositagreementonlyif(a)alloutstandingdepositarysharesissuedundertheagreementhavebeenredeemedor(b)afinaldistributioninconnectionwithanyliquidation,dissolutionorwindinguphasbeenmadetotheholdersofthedepositaryshares.

Resignation and Removal of Depositary

Thedepositarymayresignatanytimebydeliveringtousnoticeofitselectiontoresign,andwemayatanytimeremovethedepositary.Anyresignationorremovalwilltakeeffectwhenasuccessordepositaryhasbeenappointedandhasacceptedtheappointment.Appointmentmustoccurwithin

30

Page 104: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

60daysafterdeliveryofthenoticeofresignationorremoval.ThesuccessordepositarymustbeabankortrustcompanyhavingitsprincipalofficeintheUnitedStatesandhavingacombinedcapitalandsurplusofatleast$50,000,000.

Miscellaneous

Thedepositarywillforwardallreportsandcommunicationsfromuswhicharedeliveredtothedepositaryandwhichwearerequiredorotherwisedeterminetofurnishtoholdersofdebtsecuritiesorpreferredstock,asthecasemaybe.

Weandthedepositarywillnotbeliableunderthedepositagreementtoyouotherthanforourgrossnegligence,willfulmisconductorbadfaith.Neitherwenorthedepositarywillbeliableifweorthedepositaryispreventedordelayedbylaworanycircumstancebeyonditscontrolinperformingitsobligationsunderthedepositagreement.Ourandthedepositary'sobligationsunderthedepositagreementwillbelimitedtoperformanceingoodfaithofourrespectivedutiesundertheagreement.Weandthedepositarywillnotbeobligatedtoprosecuteordefendanylegalproceedingsrelatingtoanydepositaryshares,debtsecurities,commonstockorpreferredstock,asthecasemaybe,unlessasatisfactoryindemnityisfurnished.Weandthedepositarymayrelyuponwrittenadviceofcounseloraccountants,oruponinformationprovidedbypersonspresentingdebtsecuritiesorsharesofcommonstockorpreferredstock,asthecasemaybe,fordeposit,youorotherpersonsbelievedtobecompetentandondocumentswhichweandthedepositarybelievetobegenuine.

31

Page 105: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

DESCRIPTION OF WARRANTS

Thefollowingdescriptionofthewarrantsandtermsofthewarrantagreementisasummary.Itsummarizesonlythoseaspectsofthewarrantsandthoseportionsofthewarrantagreementwhichwebelievewillbemostimportanttoyourdecisiontoinvestinourwarrants.Youshouldkeepinmind,however,thatitisthewarrantagreementandthewarrantcertificaterelatingtothewarrants,andnotthissummary,whichdefinesyourrightsasawarrantholder.Theremaybeotherprovisionsinthewarrantagreementandthewarrantcertificaterelatingtothewarrantswhicharealsoimportanttoyou.Youshouldreadthesedocumentsforafulldescriptionofthetermsofthewarrants.

Wemayissuewarrantstopurchasedebtorcommonorpreferredequitysecurities.Wemayissuewarrantsindependentlyortogetherwithanyofferedsecurities.Thewarrantsmaybeattachedtoorseparatefromthoseofferedsecurities.Wewillissuethewarrantsunderwarrantagreementstobeenteredintobetweenusandabankortrustcompany,aswarrantagent,allasdescribedintheapplicableprospectussupplement.Thewarrantagentwillactsolelyasouragentinconnectionwiththewarrantsandwillnotassumeanyobligationorrelationshipofagencyortrustfororwithanyholdersorbeneficialownersofwarrants.

Theprospectussupplementrelatingtoanywarrantsthatwemayofferwillcontainthespecifictermsofthewarrants.Thesetermsmayinclude,butarenotlimitedto,thefollowing:

• thetitleofthewarrants;

• thedesignation,amountandtermsofthesecuritiesforwhichthewarrantsareexercisable;

• thedesignationandtermsoftheothersecurities,ifany,withwhichthewarrantsaretobeissuedandthenumberofwarrantsissuedwitheachothersecurity;

• thepriceorpricesatwhichthewarrantswillbeissued;

• theaggregatenumberofwarrants;

• anyprovisionsforadjustmentofthenumberoramountofsecuritiesreceivableuponexerciseofthewarrantsortheexercisepriceofthewarrants;

• thepriceorpricesatwhichthesecuritiespurchasableuponexerciseofthewarrantsmaybepurchased;

• thetermsofanymandatoryoroptionalredemptionprovisionsrelatingtothewarrants;

• thetermsofanyrightwehavetoacceleratetheexerciseofthewarrantsupontheoccurrenceofcertainevents;

• ifthewarrantswillbesoldwithanyothersecurities,andthedate,ifany,onandafterwhichthosewarrantsandanyothersecuritieswillbetransferable;

• theidentityofthewarrantagent;

• ifapplicable,thedateonandafterwhichthewarrantsandthesecuritiespurchasableuponexerciseofthewarrantswillbeseparatelytransferable;

• ifapplicable,adiscussionofthematerialU.S.federalincometaxconsiderationsapplicabletotheexerciseofthewarrants;

• anyothertermsofthewarrants,includingterms,proceduresandlimitationsrelatingtotheexchangeandexerciseofthewarrants;

• thedateonwhichtherighttoexercisethewarrantswillcommence,andthedateonwhichtherightwillexpire;

32

Page 106: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

• themaximumorminimumnumberofwarrantswhichmaybeexercisedatanytime;and

• informationwithrespecttobook-entryprocedures,ifany.

Exercise of Warrants

Eachwarrantwillentitletheholderofwarrantstopurchaseforcashtheamountofdebtorcommonorpreferredequitysecurities,attheexercisepricestatedordeterminableintheprospectussupplementforthewarrants.Warrantsmaybeexercisedatanytimeuptothecloseofbusinessontheexpirationdateshownintheprospectussupplementrelatingtothewarrants,unlessotherwisespecifiedintheapplicableprospectussupplement.Afterthecloseofbusinessontheexpirationdate,unexercisedwarrantswillbecomevoid.Warrantsmaybeexercisedasdescribedintheprospectussupplementrelatingtothewarrants.Whenthewarrantholdermakesthepaymentandproperlycompletesandsignsthewarrantcertificateatthecorporatetrustofficeofthewarrantagentoranyotherofficeindicatedintheapplicableprospectussupplement,wewill,assoonaspossible,forwardthedebtorcommonorpreferredequitysecuritiesthatthewarrantholderhaspurchased.Ifthewarrantholderexercisesthewarrantforlessthanallofthewarrantsrepresentedbythewarrantcertificate,wewillissueanewwarrantcertificatefortheremainingwarrants.

33

Page 107: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

DESCRIPTION OF PURCHASE CONTRACTS

Wemayissuefromtimetotimepurchasecontracts,includingcontractsobligatingholderstopurchasefromusandobligatingustoselltotheholders,debtsecurities,sharesofcommonstockorpreferredstock,orothersecuritiesthatmaybesoldunderthisprospectusatafuturedateordates,asthecasemaybe.Theconsiderationpayableuponsettlementofthepurchasecontracts,aswellastheprincipalamountofdebtsecuritiesornumberofsharesofcommonstock,preferredstockorothersecuritiesdeliverableuponsettlement,maybefixedatthetimethepurchasecontractsareissuedormaybedeterminedbyaformulasetforthinthepurchasecontracts.Thepurchasecontractsmaybeissuedseparatelyoraspartofunitsconsistingofapurchasecontractandothersecuritiesorobligationsissuedbyusorthirdparties,includingU.S.treasurysecurities,ineachcase,securingtheholders'obligationstopurchasetherelevantsecuritiesunderthepurchasecontracts.Thepurchasecontractsmayrequireustomakeperiodicpaymentstotheholdersofthepurchasecontractsorunitsorviceversa,andsuchpaymentsmaybeunsecuredorprefundedonsomebasis.Thepurchasecontractsmayrequireholderstosecuretheirobligationsunderthepurchasecontractsinaspecifiedmannerand,incertaincircumstances,wemaydelivernewlyissuedprepaidpurchasecontracts,oftenknownasprepaidsecurities,uponreleasetoaholderofanycollateralsecuringsuchholder'sobligationsundertheoriginalpurchasecontract.

Theapplicableprospectussupplementwilldescribethetermsofanypurchasecontracts.Thedescriptionintheapplicableprospectussupplementwillnotnecessarilybecompleteandwillbequalifiedinitsentiretybyreferencetothepurchasecontracts,and,ifapplicable,collateralarrangementsanddepositaryarrangements,relatingtothepurchasecontractsand,ifapplicable,theprepaidsecuritiesandthedocumentpursuanttowhichtheprepaidsecuritieswillbeissued.

DESCRIPTION OF UNITS

Wemayissuefromtimetotimeunitscomprisedofoneormoreoftheothersecuritiesthatmaybeofferedunderthisprospectus,inanycombination.Eachunitwillbeissuedsothattheholderoftheunitisalsotheholderofeachsecurityincludedintheunit.Thus,theholderofaunitwillhavetherightsandobligationsofaholderofeachincludedsecurity.Theunitagreementunderwhichaunitisissuedmayprovidethatthesecuritiesincludedintheunitmaynotbeheldortransferredseparatelyatanytime,oratanytimebeforeaspecifieddate.

Anyapplicableprospectussupplementwilldescribe:

• thematerialtermsoftheunitsandofthesecuritiescomprisingtheunits,includingwhetherandunderwhatcircumstancesthosesecuritiesmaybeheldortransferredseparately;

• anymaterialprovisionsrelatingtotheissuance,payment,settlement,transferorexchangeoftheunitsorofthesecuritiescomprisingtheunits;and

• anymaterialprovisionsofthegoverningunitagreementthatdifferfromthosedescribedabove.

34

Page 108: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

PLAN OF DISTRIBUTION

Wemaysellanyseriesofdebtsecurities,commonstock,preferredstock,depositoryshares,warrants,purchasecontractsandunitsbeingoffereddirectlytooneormorepurchasers,throughagents,toorthroughunderwriters,brokersordealers,orthroughacombinationofanysuchmethodsofsale.Inaddition,certainsellingstockholdersmay,fromtimetotime,offerandsellsharesofourcommonstockorpreferredstock,ineachcase,inamounts,atpricesandontermsthatwillbedeterminedatthetimeofanysuchoffering.Thedistributionofthesecuritiesmaybeeffectedfromtimetotimeinoneormoretransactionsatfixedprices,whichmaybechanged,atmarketpricesprevailingatthetimeofsale,atpricesrelatedtosuchprevailingmarketpricesoratnegotiatedprices.Wemayofferandsellsecuritiesfromtimetotimetocertainofourpensionplans.Theapplicableprospectussupplementwillsetforththetermsoftheoffering,includingthenamesofanysellingstockholders,underwriters,dealersoragents,thepurchasepriceofsuchsecuritiesandtheproceedstousand/orthesellingstockholdersfromsuchsale,anyunderwritingdiscountsandcommissionsoragencyfeesandotheritemsconstitutingunderwriters'oragents'compensation,anyinitialpublicofferingpriceandanydiscountsorconcessionsallowedorpaidtodealersoranysecuritiesexchangeonwhichsuchsecuritiesmaybelisted.Anyinitialpublicofferingprice,discountsorconcessionsallowedorpaidtodealersmaybechangedfromtimetotime.

Unlessotherwisesetforthintheapplicableprospectussupplement,theobligationsofunderwriterstopurchasetheofferedsecuritieswillbesubjecttocertainconditionsprecedent,andsuchunderwriterswillbeobligatedtopurchaseallsuchsecurities,ifanyarepurchased.ThemaximumcompensationtobereceivedbyanyparticipatingFinancialIndustryRegulatoryAuthority("FINRA")memberwillnotbegreaterthan8%forthesaleofanysecuritiesbeingregisteredpursuanttoSECRule415underthisprospectus.Unlessotherwiseindicatedintheapplicableprospectussupplement,anyagentwillbeactingonabesteffortsbasisfortheperiodofitsappointment.

Wemayenterintoderivativetransactionswiththirdparties,orsellsecuritiesnotcoveredbythisprospectustothirdpartiesinprivatelynegotiatedtransactions.Iftheapplicableprospectussupplementindicates,inconnectionwiththosederivatives,thethirdpartiesmaysellsecuritiescoveredbythisprospectusandtheapplicableprospectussupplement,includinginshortsaletransactions.Ifso,thethirdpartiesmayusesecuritiespledgedbyusorborrowedfromusorotherstosettlethosesalesortocloseoutanyrelatedopenborrowingsofstock,andmayusesecuritiesreceivedfromusinsettlementofthosederivativestocloseoutanyrelatedopenborrowingsofstock.Thethirdpartiesinsuchsaletransactionswillbeunderwritersand,ifnotidentifiedinthisprospectus,willbeidentifiedintheapplicableprospectussupplement(orapost-effectiveamendment).

Wemayalsosellsecuritiesupontheexerciseofrightsthatmaybedistributedtosecurityholders.

Undercertaincircumstances,wemayrepurchaseofferedsecuritiesandreofferthemtothepublicassetforthabove.Wemayalsoarrangeforrepurchaseandresaleofsuchofferedsecuritiesbydealers.

Wemayalsoofferandsellsecurities,ifsoindicatedintheapplicableprospectussupplement,inconnectionwitharemarketingupontheirpurchase,inaccordancewitharedemptionorrepaymentpursuanttotheirterms,orotherwise,byoneormorefirmsreferredtoasremarketingfirms,actingasprincipalsfortheirownaccountsorasouragents.Anyremarketingfirmwillbeidentifiedandthetermsofitsagreement,ifany,withusanditscompensationwillbedescribedintheapplicableprospectussupplement.RemarketingfirmsmaybedeemedtobeunderwritersundertheSecuritiesActinconnectionwiththesecuritiestheyremarket.

Wemayauthorizeunderwriters,dealersorotherpersonsactingasagentsforthemtosolicitoffersbycertaininstitutionstopurchasesecuritiesfromuspursuanttocontractsprovidingforpaymentanddeliveryonafuturedate.Institutionswithwhichsuchcontractsmaybemadeincludecommercialandsavingsbanks,insurancecompanies,pensionfunds,investmentcompanies,educationalandcharitable

35

Page 109: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

institutionsandothers,butinallcaseswemustapprovesuchinstitutions.Theobligationsofanypurchaserunderanysuchcontractwillbesubjecttotheconditionsthatthepurchaseoftheofferedsecuritiesshallnotatthetimeofdeliverybeprohibitedunderthelawsofthejurisdictiontowhichsuchpurchaserissubject.Theunderwritersandsuchotheragentswillnothaveanyresponsibilityinrespectofthevalidityorperformanceofsuchcontracts.

Inconnectionwiththeofferingofsecurities,weand/orthesellingstockholdersmaygranttotheunderwritersanoptiontopurchaseadditionalsecuritiestocoverover-allotmentsattheinitialpublicofferingprice,withanadditionalunderwritingcommission,asmaybesetforthintheapplicableprospectussupplement.Ifweand/orthesellingstockholdersgrantanyover-allotmentoption,thetermsofsuchover-allotmentoptionwillbesetforthintheprospectussupplementforsuchsecurities.

Thesecuritiesmaybeanewissueofsecuritiesthathavenoestablishedtradingmarket.Anyunderwriterstowhomsecuritiesaresoldforpublicofferingandsalemaymakeamarketinsuchsecurities,butsuchunderwriterswillnotbeobligatedtodosoandmaydiscontinueanymarketmakingatanytimewithoutnotice.Suchsecuritiesmayormaynotbelistedonanationalsecuritiesexchange.Noassurancecanbegivenastotheliquidityofortheexistenceoftradingmarketsforanysecurities.

Weand/orthesellingstockholdersmayindemnifyagents,underwriters,dealersandremarketingfirmsagainstcertainliabilities,includingliabilitiesundertheSecuritiesAct,orouragents,underwriters,dealersandremarketingfirmsmaybeentitledtocontributionwithrespecttopaymentsthatsuchpartiesmayberequiredtomakeinrespectthereof.Ouragents,underwriters,dealersandremarketingfirms,ortheiraffiliates,maybecustomersof,engageintransactionswithorperformservicesforus,intheordinarycourseofbusiness.

Anyunderwritermayengageinover-allotment,stabilizingtransactions,short-coveringtransactionsandpenaltybidsinaccordancewithRegulationMundertheExchangeAct.Over-allotmentinvolvessalesinexcessoftheofferingsize,whichcreateashortposition.Stabilizingtransactionspermitbidstopurchasetheunderlyingsecuritysolongasthestabilizingbidsdonotexceedaspecifiedmaximum.Short-coveringtransactionsinvolvepurchasesofthesecuritiesintheopenmarketafterthedistributioniscompletedtocovershortpositions.Penaltybidspermittheunderwriterstoreclaimasellingconcessionfromadealerwhenthesecuritiesoriginallysoldbythedealerarepurchasedinacoveringtransactiontocovershortpositions.Thoseactivitiesmaycausethepriceofthesecuritiestobehigherthanitwouldotherwisebe.Ifcommenced,theunderwritersmaydiscontinueanyoftheactivitiesatanytime.

Wewillidentifythespecificplanofdistribution,includinganysellingstockholders,underwriters,brokers,dealers,agentsordirectpurchasersandtheircompensationintheapplicableprospectussupplement.Incaseofanyinconsistencybetweentheinformationinthisprospectusandtheapplicableprospectussupplement,youshouldrelyontheinformationintheprospectussupplement.

36

Page 110: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

VALIDITY OF THE SECURITIES

Unlesstheapplicableprospectussupplementindicatesotherwise,thevalidityofthesecuritieswillbepasseduponforusbyourcounsel,SimpsonThacher&BartlettLLP,NewYork,NewYork.

EXPERTS

Thefinancialstatements,financialstatementschedulesandmanagement'sassessmentoftheeffectivenessofinternalcontroloverfinancialreporting(whichisincludedinManagement'sReportonInternalControlOverFinancialReporting)incorporatedinthisprospectusbyreferencetotheAnnualReportonForm10-KofCNOFinancialGroup,Inc.fortheyearendedDecember31,2017havebeensoincorporatedinrelianceonthereportsofPricewaterhouseCoopersLLP,anindependentregisteredpublicaccountingfirm,givenontheauthorityofsaidfirmasexpertsinauditingandaccounting.

37

Page 111: Barclaysd18rn0p25nwr6d.cloudfront.net/CIK-0001224608/9e5db933-0... · 2019-05-28 · income and debt to total capital ratio (excluding accumulated other comprehensive income). We

TableofContents

$425,000,000

CNO Financial Group, Inc. % Senior Notes due 2029

PROSPECTUS SUPPLEMENT

Goldman Sachs & Co. LLC Barclays

KeyBanc Capital Markets RBC Capital Markets BofA Merrill Lynch

Deutsche Bank Securities