[144] The Travelers Companies, Inc. SEC Filing

Rhea-AI Filing Summary

The Form 144 filing discloses that an affiliate of The Travelers Companies, Inc. (NYSE: TRV) intends to sell 7,742 common shares on or about 08/07/2025 through Fidelity Brokerage Services. Based on the filing’s reference price, the planned sale is valued at $2.05 million, representing roughly 0.003% of the company’s 225.1 million shares outstanding. The shares stem from stock options granted on 02/08/2022 that will be settled for cash.

The filer, identified as Andy Bessette, previously sold 5,000 shares for $1.36 million on 05/16/2025, bringing total disclosed sales within three months to 12,742 shares worth ≈$3.41 million. The filer certifies no undisclosed material adverse information and that the sale complies with Rule 144.

No financial performance data or operational updates accompany this notice; the filing strictly signals a modest insider sale that is immaterial to share count but may interest investors tracking insider trading patterns.

Insights

Corporate Governance Expert

TL;DR: Small, routine insider sale (≈$2 M) under Rule 144; immaterial to float but worth noting for sentiment.

The proposed sale of 7,742 TRV shares by executive Andy Bessette equals only 0.003% of outstanding stock and follows a 5,000-share sale in May. Aggregate insider disposition over the period totals ≈$3.4 M, insignificant relative to TRV’s market cap yet potentially indicative of personal portfolio diversification. Because the shares originate from option exercises, the transaction appears planned rather than opportunistic. No new operational information is provided, so the market impact should be limited. Overall, this is routine governance disclosure with neutral financial implications.

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

Relationship to Issuer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	7742	2050856.57	225133841	08/07/2025	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	08/07/2025	Options Granted - 02/08/2022	Issuer			7742	08/07/2025	Cash

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
Andy Bessette 485 Lexington Avenue New York NY 10017	Common	05/16/2025	5000	1363800.50

144: Remarks and Signature

Remarks

Date of Notice

ATTENTION:

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.

Signature

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)