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Travelers Companies, Inc. planned insider sales

In the last twelve months insiders at Travelers Companies, Inc. filed 57 Form 144 notices of planned sales, 514,540 shares worth $179.1 million at the time of filing, from 15 sellers. The latest, filed 4 November 2026: Olivo Maria (officer), 15,000 shares worth $6.1 million, planned for around 4 November 2026 through Fidelity Brokerage Services LLC.

FiledSellerRelationshipSharesValuePlanned saleSold, per Form 4BrokerHow acquiredFiling
4 November 2026Olivo MariaOfficer15,000$6.1 million4 November 202615,000 shares from 4 November 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
28 October 2026Bessette Andy FOfficer3,000$1.2 million28 October 20263,000 shares from 28 October 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
27 October 2026Lefebvre Mojgan MOfficer11,000$4.3 million27 October 202611,000 shares from 27 October 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
22 October 2026Rowland David DonnayOfficer5,000$2.0 million22 October 20265,000 shares from 22 October 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
22 October 2026Klenk Jeffrey P.Officer9,016$3.7 million22 October 20269,016 shares from 22 October 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
22 October 2026Toczydlowski Gregory COfficer34,771$14.0 million22 October 202634,771 shares from 22 October 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
21 October 2026Olivo MariaOfficer15,100$6.0 million21 October 202615,100 shares from 21 October 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
21 October 2026Schnitzer Alan DOfficer, Director88,900$35.3 million21 October 202688,900 shares from 21 October 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
20 October 2026Klein Michael FrederickOfficer7,500$2.9 million20 October 20267,500 shares from 20 October 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
28 August 2026Olivo MariaOfficer6,000$2.2 million28 August 20266,000 shares from 28 August 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
28 July 2026Heyman William HOfficer2,344$932,91228 July 2026No matching Form 4 saleFidelity Brokerage Services LLCRestricted Stock VestingForm 144
27 July 2026Heyman William HOfficer3,572$1.4 million27 July 2026No matching Form 4 saleFidelity Brokerage Services LLCRestricted Stock VestingForm 144
24 July 2026Kurtzman DianeOfficer4,164$1.6 million24 July 20264,164 shares from 24 July 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
24 July 2026Heyman William HOfficer5,206$2.0 million24 July 2026No matching Form 4 saleFidelity Brokerage Services LLCRestricted Stock VestingForm 144
24 July 2026Yin Daniel Tei-HwaOfficer7,153$2.8 million24 July 20267,153 shares from 24 July 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
23 July 2026Thomsen Laurie JFormer Director1,396$527,60323 July 2026No matching Form 4 saleFidelity Brokerage Services LLCRestricted Stock VestingForm 144
22 July 2026Munson Paul E.Officer1,525$564,10522 July 20261,525 shares from 22 July 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
22 July 2026Bessette Andy FOfficer3,000$1.1 million22 July 20263,000 shares from 22 July 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
22 July 2026Heyman William HOfficer4,701$1.7 million22 July 2026No matching Form 4 saleFidelity Brokerage Services LLCRestricted Stock VestingForm 144
22 July 2026Rowland David DonnayOfficer5,000$1.9 million22 July 20265,000 shares from 22 July 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
21 July 2026Klein Michael FrederickOfficer6,000$2.2 million21 July 20266,000 shares from 21 July 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
21 July 2026Heyman William HOfficer8,000$2.9 million21 July 2026No matching Form 4 saleFidelity Brokerage Services LLCStock Option ExerciseForm 144
21 July 2026Frey Daniel S.Officer14,037$5.2 million21 July 202614,037 shares from 21 July 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
21 July 2026Lefebvre Mojgan MOfficer16,313$6.0 million21 July 202616,313 shares from 21 July 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
26 May 2026Klein Michael FrederickOfficer10,000$3.1 million26 May 202610,000 shares from 26 May 2026Fidelity Brokerage Services LLCOption Granted - 02/04/2020Form 144
22 May 2026Bessette Andy FOfficer4,255$1.3 million22 May 20264,255 shares from 22 May 2026Fidelity Brokerage Services LLCOption Granted - 02/07/2023Form 144
28 April 2026Heyman William HOfficer1,557$483,67028 April 20261,557 shares from 28 April 2026Fidelity Brokerage Services LLCOption Granted - 02/07/2023Form 144
28 April 2026Kess Avrohom J.Officer6,735$2.1 million28 April 20266,735 shares from 28 April 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
20 April 2026Kurtzman DianeOfficer2,867$869,98020 April 20262,867 shares from 20 April 2026Fidelity Brokerage Services LLCOption Granted - 02/04/2020; Restricted Stock VestingForm 144
20 April 2026Klenk Jeffrey P.Officer6,414$2.0 million20 April 20266,414 shares from 20 April 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
20 April 2026Klein Michael FrederickOfficer10,000$3.0 million20 April 202610,000 shares from 20 April 2026Fidelity Brokerage Services LLCOptions Granted - 02/04/2020Form 144
26 February 2026Rowland David DonnayOfficer4,731$1.5 million26 February 20264,731 shares from 26 February 2026Fidelity Brokerage Services LLCOptions Granted - 02/05/2019Form 144
26 February 2026Olivo MariaOfficer10,400$3.2 million26 February 202610,400 shares from 26 February 2026Fidelity Brokerage Services LLCOption Granted - 02/09/2017Form 144
25 February 2026Munson Paul E.Officer3,727$1.1 million25 February 20263,727 shares from 25 February 2026Fidelity Brokerage Services LLCOption Granted - 02/05/2019; Restricted Stock VestingForm 144
23 February 2026Heyman William HOfficer4,000$1.2 million23 February 20264,000 shares from 23 February 2026Fidelity Brokerage Services LLCOption Granted - 02/07/2023; Option Granted - 02/08/2022Form 144
20 February 2026Heyman William HOfficer1,000$304,00020 February 20261,000 shares from 20 February 2026Fidelity Brokerage Services LLCOption Granted - 02/08/2022Form 144
20 February 2026Kess Avrohom J.Officer4,756$1.4 million20 February 20264,756 shares from 20 February 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
20 February 2026Frey Daniel S.Officer8,000$2.4 million20 February 20268,000 shares from 20 February 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
20 February 2026Toczydlowski Gregory COfficer12,200$3.7 million20 February 202612,200 shares from 20 February 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
19 February 2026Lefebvre Mojgan MOfficer5,827$1.7 million19 February 20265,827 shares from 19 February 2026Fidelity Brokerage Services LLCRestricted Stock VestingForm 144
17 February 2026Heyman William HOfficer1,000$300,00017 February 20261,000 shares from 17 February 2026Fidelity Brokerage Services LLCOption Granted - 02/08/2022Form 144
17 February 2026Bessette Andy FOfficer6,000$1.8 million17 February 20266,000 shares from 17 February 2026Fidelity Brokerage Services LLCOption Granted 02/07/2023Form 144
6 February 2026Heyman William HOfficer1,000$303,0006 February 20266,000 shares from 5 February 2026Fidelity Brokerage Services LLCOption Granted - 02/08/2022Form 144
6 February 2026Klein Michael FrederickOfficer10,000$3.0 million6 February 202610,000 shares from 6 February 2026Fidelity Brokerage Services LLCOptions Granted - 02/04/2020Form 144
6 February 2026Olivo MariaOfficer10,400$3.1 million6 February 202610,400 shares from 6 February 2026Fidelity Brokerage Services LLCOptions Granted - 02/09/2017Form 144
5 February 2026Heyman William HOfficer5,000$1.5 million5 February 2026No matching Form 4 saleFidelity Brokerage Services LLCOption Granted 02/08/2022Form 144
4 February 2026Schnitzer Alan DOfficer, Director55,733$16.4 million4 February 202655,733 shares from 4 February 2026Fidelity Brokerage Services LLCStock Option ExerciseForm 144
23 January 2026Klenk Jeffrey P.Officer16,712$4.7 million23 January 202616,712 shares from 23 January 2026Fidelity Brokerage Services LLCOptions Granted - 02/04/2020; Options Granted - 02/06/2018Form 144
26 November 2025Olivo MariaOfficer8,920$2.6 million26 November 20258,920 shares from 26 November 2025Fidelity Brokerage Services LLCOption Granted - 02/09/2017Form 144
25 November 2025Heyman William HOfficer4,000$1.2 million25 November 20254,000 shares from 25 November 2025Fidelity Brokerage Services LLCOption Granted 02/08/2022Form 144
24 November 2025Kurtzman DianeOfficer4,805$1.4 million24 November 20254,805 shares from 24 November 2025Fidelity Brokerage Services LLCOption Granted - 02/05/2019Form 144
21 November 2025Heyman William HOfficer2,000$583,00021 November 20252,000 shares from 21 November 2025Fidelity Brokerage Services LLCOption Granted - 02/08/2022Form 144
21 November 2025Rowland David DonnayOfficer5,000$1.5 million21 November 20255,000 shares from 21 November 2025Fidelity Brokerage Services LLCOption Granted - 02/05/2019Form 144
13 November 2025Heyman William HOfficer1,803$522,06713 November 20253,803 shares from 12 November 2025Fidelity Brokerage Services LLCOption Granted - 02/08/2022Form 144
12 November 2025Heyman William HOfficer2,000$575,00012 November 2025No matching Form 4 saleFidelity Brokerage Services LLCOption Granted - 02/02/2021Form 144
12 November 2025Heyman William HOfficer4,000$1.1 million11 November 20254,000 shares from 11 November 2025Fidelity Brokerage Services LLCOption Granted - 02/02/2021Form 144
10 November 2025Heyman William HOfficer2,000$563,00010 November 20252,000 shares from 10 November 2025Fidelity Brokerage Services LLCOption Granted - 02/02/2021Form 144
A Form 144 is the notice an insider files with the SEC before selling restricted or control shares over the Rule 144 thresholds; it says what may be sold, not what was.
Read moreValue is the filer's own aggregate market value. Sold, per Form 4: the same seller's open-market sales on Form 4 from the notice's date to 90 days after, added up, as they appear on the insiders page; a holder who files no Form 4, such as some large holders, never shows one. What is a Form 144?