WHITE MOUNTAINS INSURANCE GROUP LTD (WTM)

Latest Insider Confidence Score

2026Q1

44.3
Bearish

Company insider confidence (by quarter)

2009Q1 2026Q1

Largest shareholders

Insider Role (last 12 mo) Shares held Filed at
White Mountains Insurance Group Ltd 10% Owner 17,856,614 May 9, 2024
WM Hinson (Bermuda) Ltd. 10% Owner 17,856,614 May 9, 2024
Byrne John Joseph Other 637,117 Feb 6, 2013
Barrette Raymond Joseph Rene CEO 104,411 May 28, 2010
Davis Morgan W Director 17,259 Nov 30, 2018

Recent buy/sell transactions

Exec date Filing date Insider Role Signal Confidence Shares % of shares Under plan? Amount (USD)
Mar 4, 2026 Mar 5, 2026 Tanner David Allen Director Neutral 27.5 -225 -10.69% ✗ -
Feb 25, 2026 Feb 27, 2026 Caffrey Liam P CEO Neutral 90.0 +1,500 39.34% ✗ -
Feb 25, 2026 Feb 27, 2026 Harrison Giles E President Neutral 90.0 +775 40.75% ✗ -
Feb 25, 2026 Feb 27, 2026 Hildreth Michaela MD & Chief Accounting Officer Neutral 90.0 +600 16.06% ✗ -
Feb 25, 2026 Feb 27, 2026 Papamichael Michael A CFO Neutral 90.0 +500 33.69% ✗ -
Feb 25, 2026 Feb 27, 2026 SEELIG ROBERT LAWRENCE EVP & General Counsel Neutral 82.5 +775 3.83% ✗ -
Jan 1, 2026 Jan 5, 2026 Hildreth Michaela MD & Chief Accounting Officer Sell 20.0 -274 -6.83% ✗ $569.4K
Jan 1, 2026 Jan 2, 2026 Papamichael Michael A CFO Sell 20.0 -131 -8.11% ✗ $272.2K
Jan 2, 2026 Papamichael Michael A CFO Neutral 52.5 - 0.00% ✗ -
Jan 1, 2026 Jan 2, 2026 SEELIG ROBERT LAWRENCE EVP & General Counsel Sell 20.0 -398 -1.93% ✗ $827.1K
Jan 1, 2026 Jan 2, 2026 Caffrey Liam P CEO Sell 20.0 -425 -10.03% ✗ $883.2K
Dec 23, 2025 Dec 23, 2025 Hildreth Michaela MD & Chief Accounting Officer Neutral 27.5 -60 -1.47% ✗ -
Dec 19, 2025 Dec 22, 2025 CAMPBELL REID TARLTON Director Sell 15.0 -5,000 -32.14% ✗ $10.3M
Dec 19, 2025 Dec 22, 2025 CAMPBELL REID TARLTON Director Neutral 27.5 -5,000 -32.14% ✗ -
Dec 19, 2025 Dec 22, 2025 Rountree George Manning CEO Sell 15.0 -5,000 -20.53% ✗ $10.3M
Dec 16, 2025 Dec 16, 2025 Gelston Philip A Director Sell 20.0 -165 -9.52% ✗ $338K
Nov 25, 2025 Nov 26, 2025 CAMPBELL REID TARLTON Director Neutral 45.0 -50 -0.32% ✗ -
Nov 10, 2025 Nov 10, 2025 Tanner David Allen Director Neutral 52.5 -4 -0.19% ✗ -
May 22, 2025 May 27, 2025 SHANK SUZANNE F. Director Neutral 90.0 +150 20.80% ✗ -
May 22, 2025 May 23, 2025 Yi Steven Director Neutral 90.0 +150 40.00% ✗ -
May 22, 2025 May 23, 2025 Tanner David Allen Director Neutral 85.0 +150 7.66% ✗ -
May 22, 2025 May 23, 2025 Hicks Weston M Director Neutral 85.0 +210 8.28% ✗ -
May 22, 2025 May 23, 2025 Gelston Philip A Director Neutral 85.0 +150 9.48% ✗ -
May 22, 2025 May 23, 2025 Dillon Margaret Director Neutral 90.0 +150 18.87% ✗ -
May 22, 2025 May 23, 2025 CHOKSI MARY C Director Neutral 85.0 +150 8.78% ✗ -
May 22, 2025 May 23, 2025 Carlson Peter M Director Neutral 90.0 +150 26.46% ✗ -
May 22, 2025 May 23, 2025 CAMPBELL REID TARLTON Director Neutral 67.5 +150 0.97% ✗ -
Feb 26, 2025 Feb 28, 2025 Rountree George Manning CEO Neutral 85.0 +1,625 7.15% ✗ -
Feb 26, 2025 Feb 28, 2025 Caffrey Liam P CFO Neutral 90.0 +1,025 31.92% ✗ -
Feb 26, 2025 Feb 28, 2025 Harrison Giles E EVP & Chief Strategy Officer Neutral 90.0 +900 90.00% ✗ -
Feb 26, 2025 Feb 28, 2025 SEELIG ROBERT LAWRENCE EVP & General Counsel Neutral 82.5 +825 4.17% ✗ -
Feb 26, 2025 Feb 28, 2025 Hildreth Michaela MD & Chief Accounting Officer Neutral 90.0 +625 18.15% ✗ -
Jan 1, 2025 Jan 3, 2025 Rountree George Manning CEO Sell 17.5 -1,067 -4.48% ✗ $2.1M
Jan 1, 2025 Jan 3, 2025 Caffrey Liam P CFO Sell 20.0 -420 -11.57% ✗ $816.9K
Jan 1, 2025 Jan 3, 2025 SEELIG ROBERT LAWRENCE EVP & General Counsel Sell 20.0 -496 -2.45% ✗ $964.7K
Jan 1, 2025 Jan 3, 2025 Hildreth Michaela MD & Chief Accounting Officer Sell 20.0 -323 -8.58% ✗ $628.3K
Nov 29, 2024 Dec 2, 2024 Hildreth Michaela MD & Chief Accounting Officer Neutral 27.5 -75 -1.95% ✗ -
Jun 10, 2024 Jun 10, 2024 Harrison Giles E EVP & Chief Strategy Officer Neutral 90.0 +1,000 100.00% ✗ -
Jun 10, 2024 Harrison Giles E EVP & Chief Strategy Officer Neutral 52.5 - 0.00% ✗ -
May 23, 2024 May 24, 2024 Yi Steven Director Neutral 90.0 +165 78.57% ✗ -
May 23, 2024 May 24, 2024 Tanner David Allen Director Neutral 85.0 +165 9.20% ✗ -
May 23, 2024 May 24, 2024 SHANK SUZANNE F. Director Neutral 90.0 +165 29.68% ✗ -
May 23, 2024 May 24, 2024 Gelston Philip A Director Neutral 90.0 +165 11.64% ✗ -
May 23, 2024 May 24, 2024 Dillon Margaret Director Neutral 90.0 +165 26.19% ✗ -
May 23, 2024 May 24, 2024 CHOKSI MARY C Director Neutral 90.0 +165 10.69% ✗ -
May 23, 2024 May 24, 2024 Carlson Peter M Director Neutral 90.0 +165 17.05% ✗ -
May 23, 2024 May 24, 2024 CAMPBELL REID TARLTON Director Neutral 77.5 +165 1.08% ✗ -
May 23, 2024 May 24, 2024 Hicks Weston M Director Neutral 85.0 +230 9.97% ✗ -
May 7, 2024 May 9, 2024 WHITE MOUNTAINS INSURANCE GROUP LTD 10% Owner Sell 15.0 -5,000,200 -21.88% ✗ $95M
Mar 21, 2024 Mar 21, 2024 CAMPBELL REID TARLTON Director Neutral 45.0 -55 -0.36% ✗ -
Feb 22, 2024 Feb 23, 2024 Rountree George Manning CEO Neutral 85.0 +1,800 8.18% ✗ -
Feb 22, 2024 Feb 23, 2024 Caffrey Liam P CFO Neutral 90.0 +1,125 44.95% ✗ -
Feb 22, 2024 Feb 23, 2024 SEELIG ROBERT LAWRENCE EVP & General Counsel Neutral 82.5 +900 4.64% ✗ -
Feb 22, 2024 Feb 23, 2024 Hildreth Michaela MD & Chief Accounting Officer Neutral 90.0 +600 18.53% ✗ -
Feb 22, 2024 Feb 23, 2024 CAMPBELL REID TARLTON Director Neutral 60.0 +45 0.29% ✗ -
Jan 1, 2024 Jan 2, 2024 Rountree George Manning CEO Sell 17.5 -1,068 -4.63% ✗ $1.6M
Jan 1, 2024 Jan 2, 2024 CAMPBELL REID TARLTON President Sell 17.5 -710 -4.43% ✗ $1.1M
Jan 1, 2024 Jan 2, 2024 SEELIG ROBERT LAWRENCE EVP & General Counsel Sell 20.0 -399 -2.02% ✗ $600.5K
Jan 1, 2024 Jan 2, 2024 Hildreth Michaela MD & Chief Accounting Officer Sell 20.0 -261 -7.46% ✗ $392.8K
Dec 1, 2023 Dec 1, 2023 Hildreth Michaela MD & Chief Accounting Officer Neutral 27.5 -100 -2.78% ✗ -
Nov 17, 2023 Nov 20, 2023 Hicks Weston M Director Buy 100.0 +1,000 76.57% ✗ $1.5M
Nov 17, 2023 Nov 20, 2023 Hicks Weston M Director Buy 100.0 +1,000 76.57% ✗ $1.5M
Jun 30, 2023 Jun 30, 2023 WHITE MOUNTAINS INSURANCE GROUP LTD Director Buy 100.0 +5,916,816 34.93% ✗ $59.2M
May 25, 2023 May 30, 2023 Carlson Peter M Director Neutral 90.0 +180 22.84% ✗ -
May 25, 2023 May 26, 2023 Dillon Margaret Director Neutral 90.0 +180 40.00% ✗ -
May 25, 2023 May 26, 2023 Tanner David Allen Director Neutral 90.0 +180 11.16% ✗ -
May 25, 2023 May 26, 2023 SHANK SUZANNE F. Director Neutral 90.0 +180 47.87% ✗ -
May 25, 2023 May 26, 2023 Gelston Philip A Director Neutral 90.0 +180 14.54% ✗ -
May 25, 2023 May 26, 2023 CHOKSI MARY C Director Neutral 90.0 +180 13.21% ✗ -
May 25, 2023 May 26, 2023 Hicks Weston M Director Neutral 90.0 +250 23.67% ✗ -
May 25, 2023 May 26, 2023 Yi Steven Director Neutral 90.0 +180 600.00% ✗ -
May 26, 2023 Yi Steven Director Neutral 52.5 - 0.00% ✗ -
Feb 22, 2023 Feb 24, 2023 Rountree George Manning CEO Neutral 85.0 +2,000 9.50% ✗ -
Feb 22, 2023 Feb 24, 2023 Caffrey Liam P CFO Neutral 90.0 +1,250 100.00% ✗ -
Feb 22, 2023 Feb 24, 2023 SEELIG ROBERT LAWRENCE EVP & General Counsel Neutral 85.0 +1,000 5.33% ✗ -
Feb 22, 2023 Feb 24, 2023 Hildreth Michaela MD & Chief Accounting Officer Neutral 90.0 +600 20.03% ✗ -
Feb 22, 2023 Feb 23, 2023 Hicks Weston M Director Neutral 85.0 +56 5.60% ✗ -
Feb 23, 2023 Hicks Weston M Director Neutral 52.5 - 0.00% ✗ -
Jan 1, 2023 Jan 3, 2023 Rountree George Manning CEO Sell 17.5 -1,068 -4.83% ✗ $1.5M
Jan 1, 2023 Jan 3, 2023 CAMPBELL REID TARLTON President Sell 17.5 -710 -4.25% ✗ $1M
Jan 1, 2023 Jan 3, 2023 SEELIG ROBERT LAWRENCE EVP & General Counsel Sell 20.0 -359 -1.88% ✗ $507.7K
Jan 1, 2023 Jan 3, 2023 Hildreth Michaela MD & Chief Accounting Officer Sell 22.5 -176 -5.55% ✗ $248.9K
Dec 28, 2022 Dec 29, 2022 DAVIS MORGAN W Director Neutral 27.5 -200 -2.52% ✗ -
Dec 28, 2022 Dec 29, 2022 Hildreth Michaela MD & Chief Accounting Officer Neutral 27.5 -53 -1.64% ✗ -
Dec 22, 2022 Dec 27, 2022 Hildreth Michaela MD & Chief Accounting Officer Sell 22.5 -100 -3.01% ✗ $137.2K
Sep 20, 2022 Sep 22, 2022 Carlson Peter M Director Sell 20.0 -200 -20.24% ✗ $280K
Sep 20, 2022 Sep 22, 2022 DAVIS MORGAN W Director Sell 17.5 -945 -10.64% ✗ $1.3M
Jun 1, 2022 Jun 2, 2022 CAMPBELL REID TARLTON President Neutral 37.5 -100 -0.59% ✗ -
May 31, 2022 Jun 1, 2022 Hildreth Michaela MD & Chief Accounting Officer Sell 22.5 -100 -2.92% ✗ $127.1K
May 26, 2022 May 27, 2022 DAVIS MORGAN W Director Neutral 82.5 +315 3.68% ✗ -
May 26, 2022 May 27, 2022 Dillon Margaret Director Neutral 90.0 +225 100.00% ✗ -
May 26, 2022 May 27, 2022 Gelston Philip A Director Neutral 90.0 +225 22.21% ✗ -
May 26, 2022 May 27, 2022 Carlson Peter M Director Neutral 90.0 +225 29.49% ✗ -
May 26, 2022 May 27, 2022 CHOKSI MARY C Director Neutral 90.0 +225 19.77% ✗ -
May 26, 2022 May 27, 2022 Tanner David Allen Director Neutral 90.0 +225 16.21% ✗ -
May 26, 2022 May 27, 2022 SHANK SUZANNE F. Director Neutral 90.0 +225 149.01% ✗ -
May 16, 2022 May 17, 2022 SEELIG ROBERT LAWRENCE EVP & General Counsel Neutral 52.5 -25 -0.13% ✗ -
Mar 7, 2022 Caffrey Liam P CFO Neutral 52.5 - 0.00% ✗ -
Feb 25, 2022 Feb 28, 2022 Rountree George Manning CEO Neutral 90.0 +2,700 13.90% ✗ -
Feb 25, 2022 Feb 28, 2022 SEELIG ROBERT LAWRENCE EVP & General Counsel Neutral 90.0 +2,000 11.66% ✗ -