WTM · White Mountains Insurance Group Ltd · Insider Trading
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Trades by corporate insiders — officers, directors and holders of more than 10% of the shares — disclosed to the SEC on Forms 4 and 5. Form 3 supplies initial ownership rather than a trade; Form 4 must be filed within two business days of the trade.
| Date | Insider | Role | Type | Security | Shares |
|---|---|---|---|---|---|
| 2026-08-31 | Tanner David Allen |
Director |
Gift↓
|
Common Shares
|
2 |
| 2026-08-26 | Klar Stephen |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Pro-rated Annual Director Share Award |
Common Shares
|
113 |
| 2026-05-21 | SHANK SUZANNE F. |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
135 |
| 2026-05-21 | Tanner David Allen |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
135 |
| 2026-05-21 | Dillon Margaret |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
135 |
| 2026-05-21 | Carlson Peter M |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
135 |
| 2026-05-21 | CAMPBELL REID TARLTON |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
135 |
| 2026-05-21 | CHOKSI MARY C |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
135 |
| 2026-05-21 | Gelston Philip A |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
135 |
| 2026-05-21 | Hicks Weston M |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Chairman Share Award |
Common Shares
|
190 |
| 2026-05-21 | Chu John |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
135 |
| 2026-03-19 | SEELIG ROBERT LAWRENCE |
EVP & General Counsel |
Gift↓
|
Common Shares
|
50 |
| 2026-03-04 | Tanner David Allen |
Director |
Gift↓
|
Common Shares
|
225 |
| 2026-02-25 | Harrison Giles E |
President |
Award↑
Filing footnotes — Common Shares (restricted) (Direct)
On February 25, 2026, the Reporting Person received a restricted share award of 775 Common Shares, which vests on January 1, 2029. |
Common Shares (restricted)
|
775 |
| 2026-02-25 | Hildreth Michaela |
MD & Chief Accounting Officer |
Award↑
Filing footnotes — Common Shares (Restricted) (Direct)
On February 25, 2026, the Reporting Person received a restricted share award of 600 Common Shares, which vests on January 1, 2029. |
Common Shares (Restricted)
|
600 |
| 2026-02-25 | Papamichael Michael A |
Chief Financial Officer |
Award↑
Filing footnotes — Common Shares (Restricted) (Direct)
On February 25, 2026, the Reporting Person received a restricted share award of 500 Common Shares, which vests on January 1, 2029. |
Common Shares (Restricted)
|
500 |
| 2026-02-25 | Caffrey Liam P |
Director, Chief Executive Officer |
Award↑
Filing footnotes — Common Shares (Restricted) (Direct)
On February 25, 2026, the Reporting Person received a restricted share award of 1,500 Common Shares, which vests on January 1, 2029. |
Common Shares (Restricted)
|
1,500 |
| 2026-02-25 | SEELIG ROBERT LAWRENCE |
EVP & General Counsel |
Award↑
Filing footnotes — Common Shares (restricted) (Direct)
On February 25, 2026, the Reporting Person received a restricted share award of 775 Common Shares, which vests on January 1, 2029. |
Common Shares (restricted)
|
775 |
| 2026-01-01 | Hildreth Michaela |
MD & Chief Accounting Officer |
Tax↓
Filing footnotes — Common Shares (Direct)
On January 1, 2026, 600 restricted Common Shares became unrestricted. 274 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations. |
Common Shares
|
274 |
| 2026-01-01 | SEELIG ROBERT LAWRENCE |
EVP & General Counsel |
Tax↓
Filing footnotes — Common Shares (Direct)
On January 1, 2026, 1,000 restricted Common Shares became unrestricted. 398 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations. |
Common Shares
|
398 |
| 2026-01-01 | Caffrey Liam P |
Director, Chief Executive Officer |
Tax↓
Filing footnotes — Common Shares (Direct)
On January 1, 2026, 1,250 restricted Common Shares became unrestricted. 425 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations. |
Common Shares
|
425 |
| 2026-01-01 | Papamichael Michael A |
Chief Financial Officer |
Tax↓
Filing footnotes — Common Shares (Direct)
On January 1, 2026, 400 restricted Common Shares became unrestricted. 131 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations. |
Common Shares
|
131 |
| 2025-12-23 | Hildreth Michaela |
MD & Chief Accounting Officer |
Gift↓
|
Common Shares
|
60 |
| 2025-12-19 | CAMPBELL REID TARLTON |
Director |
Sell↓
|
Common Shares
|
5,000 |
| 2025-12-19 | Rountree George Manning |
Director, Chief Executive Officer |
Sell↓
|
Common Shares
|
5,000 |
| 2025-12-16 | Gelston Philip A |
Director |
Sell↓
|
Common Shares
|
165 |
| 2025-11-25 | CAMPBELL REID TARLTON |
Director |
Gift↓
|
Common Shares
|
50 |
| 2025-11-10 | Tanner David Allen |
Director |
Gift↓
|
Common Shares
|
4 |
| 2025-05-22 | Hicks Weston M |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Chairman Share Award |
Common Shares
|
210 |
| 2025-05-22 | Gelston Philip A |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
150 |
| 2025-05-22 | SHANK SUZANNE F. |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
150 |
| 2025-05-22 | Tanner David Allen |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
150 |
| 2025-05-22 | CAMPBELL REID TARLTON |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
150 |
| 2025-05-22 | Dillon Margaret |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
150 |
| 2025-05-22 | Yi Steven |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
150 |
| 2025-05-22 | CHOKSI MARY C |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
150 |
| 2025-05-22 | Carlson Peter M |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award Since the date of the reporting person's last ownership report, he transferred 566 shares of WTM common stock in connection with a dissolution of marriage. The reporting person no longer reports as beneficially owned any such transferred securities. |
Common Shares
|
150 |
| 2025-02-26 | Rountree George Manning |
Director, Chief Executive Officer |
Award↑
Filing footnotes — Common Shares (restricted) (Direct)
On February 26, 2025, the Reporting Person received a restricted share award of 1,625 Common Shares, which vests on January 1, 2028. |
Common Shares (restricted)
|
1,625 |
| 2025-02-26 | SEELIG ROBERT LAWRENCE |
EVP & General Counsel |
Award↑
Filing footnotes — Common Shares (restricted) (Direct)
On February 26 2025, the Reporting Person received a restricted share award of 825 Common Shares, which vests on January 1, 2028. |
Common Shares (restricted)
|
825 |
| 2025-02-26 | Harrison Giles E |
President |
Award↑
Filing footnotes — Common Shares (restricted) (Direct)
On February 26, 2025, the Reporting Person received a restricted share award of 900 Common Shares, which vests on January 1, 2028. |
Common Shares (restricted)
|
900 |
| 2025-02-26 | Caffrey Liam P |
Director, Chief Executive Officer |
Award↑
Filing footnotes — Common Shares (restricted) (Direct)
On February 26, 2025, the Reporting Person received a restricted share award of 1,025 Common Shares, which vests on January 1, 2028. |
Common Shares (restricted)
|
1,025 |
| 2025-02-26 | Hildreth Michaela |
MD & Chief Accounting Officer |
Award↑
Filing footnotes — Common Shares (Restricted) (Direct)
On February 26, 2025, the Reporting Person received a restricted share award of 625 Common Shares, which vests on January 1, 2028. |
Common Shares (Restricted)
|
625 |
| 2025-01-01 | Caffrey Liam P |
Director, Chief Executive Officer |
Tax↓
Filing footnotes — Common Shares (Direct)
On January 1, 2025, 1,250 restricted Common Shares became unrestricted. 420 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations. |
Common Shares
|
420 |
| 2025-01-01 | SEELIG ROBERT LAWRENCE |
EVP & General Counsel |
Tax↓
Filing footnotes — Common Shares (Direct)
On January 1, 2025, 1,250 restricted Common Shares became unrestricted. 496 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations. |
Common Shares
|
496 |
| 2025-01-01 | Hildreth Michaela |
MD & Chief Accounting Officer |
Tax↓
Filing footnotes — Common Shares (Direct)
On January 1, 2025, 750 restricted Common Shares became unrestricted. 323 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations. |
Common Shares
|
323 |
| 2025-01-01 | Rountree George Manning |
Director, Chief Executive Officer |
Tax↓
Filing footnotes — Common Shares (Direct)
On January 1, 2025, 2,700 restricted Common Shares became unrestricted. 1,067 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations. |
Common Shares
|
1,067 |
| 2024-11-29 | Hildreth Michaela |
MD & Chief Accounting Officer |
Gift↓
|
Common Shares
|
75 |
| 2024-06-10 | Harrison Giles E |
President |
Award↑
Filing footnotes — Common Shares (restricted) (Direct)
On June 10, 2024, the Reporting Person received a restricted share award of 1,000 Common Shares, which vests on January 1, 2027. |
Common Shares (restricted)
|
1,000 |
| 2024-05-23 | Tanner David Allen |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Director Share Award |
Common Shares
|
165 |
| 2024-05-23 | Hicks Weston M |
Director |
Award↑
Filing footnotes — Common Shares (Direct)
Annual Chairman Share Award |
Common Shares
|
230 |