$750,000,000 4.950% Senior Notes due 2031 We are offering $750,000,000 aggregate principal amount of 4.950% senior notes due 2031 (the “senior notes”). Interest on the senior notes ispayable semi-annually in arrears on January 24 and July24 of each year, beginning on January 24, 2027. The senior notes will mature on July 24, 2031.Prior to June24, 2031 (the date that is one month prior to the maturity date of the senior notes), we may redeem the senior notes, in whole or in part, atany time at the “make-whole” redemption price described herein. On or after June24, 2031 (the date that is one month prior to the maturity date of thesenior notes), we may redeem the senior notes, in whole or in part, at any time at a redemption price equal to 100% of the principal amount of any seniornotes to be redeemed plus accrued and unpaid interest to, but excluding, the redemption date, as described herein. The senior notes will be unsecured senior obligations of our company and will rank equally with all of our other unsecured senior indebtednessfrom time to time outstanding. The senior notes will be issued only in registered form in denominations of $2,000 and integral multiples of $1,000 inexcess thereof. Investing in the senior notes involves risks. See “A Special Note RegardingForward-Looking Statements”beginning on page S-4, “Risk Factors” contained in our Annual Report on Form 10-K for the year ended December 31,2025 and other information included or incorporated by reference in this prospectus supplement and the accompanyingprospectus for a discussion of the factors you should carefully consider before deciding to purchase any senior notes. Neither the Securities and Exchange Commission nor any other regulatory body has approved or disapproved of these securities orpassed upon the accuracy or adequacy of this prospectus supplement or the accompanying prospectus. Any representation to the contrary is acriminal offense. PerNoteTotalPublic Offering Price(1)99.978%$749,835,000Underwriting Discount0.450%$3,375,000Proceeds to The Travelers Companies, Inc. (before expenses)99.528%$746,460,000 (1)Plus accrued interest, if any, from and including July 24, 2026, if settlement occurs after that date. The underwriters expect to deliver the senior notes to investors on or about July 24, 2026, in book-entry form only through the facilities of TheDepository Trust Company for the accounts of its participants, including Clearstream Banking S.A., Luxembourg and Euroclear Bank SA/NV. We have not, and the underwriters have not, authorized anyone to provide you with any information other than that contained or incorporatedby reference in this prospectus supplement, the accompanying prospectus and any related free writing prospectus issued by us. We and theunderwriters take no responsibility for, and can provide no assurance as to the reliability of, any information that others may provide to you.We are not, and the underwriters are not, making an offer to sell these securities in any jurisdiction where the offer is not permitted. You shouldnot assume that the information contained in this prospectus supplement, the accompanying prospectus, the documents incorporated byreference or any related free writing prospectus issued by us is accurate as of any date other than their respective dates. Our business, financialcondition, results of operations or prospects may have changed since those dates. TABLE OF CONTENTSProspectus Supplement About This Prospectus SupplementWhere You Can Find More InformationSummaryA Special Note Regarding Forward-Looking StatementsUse of ProceedsCapitalizationDescription of the Senior NotesMaterial U.S. Federal Income Tax ConsequencesCertain ERISA ConsiderationsUnderwritingLegal MattersExperts Prospectus About This ProspectusA Special Note Regarding Forward-Looking StatementsWhere You Can Find More InformationThe Travelers Companies, Inc.The TrustsRisk FactorsUse of ProceedsDescription of Debt Securities We May OfferDescription of Preferred Stock We May OfferDescription of Depositary Shares We May OfferDescription of Our Common StockDescription of Warrants We May OfferDescription of Stock Purchase Contracts We May OfferDescription of Units We May OfferDescription of Preferred Securities That the Trusts May OfferDescription of Trust GuaranteesMaterial United States Federal Income Tax ConsequencesCertain ERISA MattersValidity of SecuritiesExperts ABOUT THIS PROSPECTUS SUPPLEMENT This document is in two parts. The first part is this prospectus supplement, which describes the specific terms of this offering and other mattersrelating to us and our financial condition. The second part, the accompanying prospectus, gives more general information about securities we may offerfrom time to time, some of which may not apply to this offering. If information varies between this prospectus supplement and the accompanying prospectus or the documents incorporated by reference, youshould rely on the information in t