| Date | Insider | Title | Code | Shares | Price | Value |
|---|---|---|---|---|---|---|
| May 18, 2026 | BROWN DAVID A | Director | S | 37,300 | $32.1623 | $1.20M |
| May 15, 2026 | BROWN DAVID A | Director | S | 12,700 | $31.8202 | $404.12K |
| May 13, 2026 | Levenson Jonathan B. | Group Treasurer | S | 6,075 | $30.6100 | $185.96K |
| May 8, 2026 | Levenson Jonathan B. | Group Treasurer | S | 3,030 | $30.6700 | $92.93K |
| May 5, 2026 | Green Karen Ann | Director | F | 3,378 | $30.4300 | $102.79K |
| May 5, 2026 | Green Karen Ann | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | BROWN DAVID A | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | Priebe David | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | Wilson Peter W | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | Simmons Everard Barclay | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | Karna Anu | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | Gauthier John J | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | Pestcoe Marvin | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | Deegan Brian John | Group Chief Accounting Officer | S | 11,000 | $30.6949 | $337.64K |
| May 5, 2026 | Patterson Alan Neil | Director | A | 4,929 | $0.0000 | $0.00 |
| May 5, 2026 | Vaughan Therese M | Director | A | 4,929 | $0.0000 | $0.00 |
| Apr 8, 2026 | COOPER BRADLEY E | Director | P | 99 | $31.0100 | $3.07K |
| Mar 2, 2026 | Albo Giuseppina | Chief Executive Officer | A | 81,015 | $0.0000 | $0.00 |
| Mar 2, 2026 | Albo Giuseppina | Chief Executive Officer | F | 37,818 | $31.5900 | $1.19M |
| Mar 2, 2026 | Fisher Daniel Mark | Group Head of HR & Comm. | A | 10,882 | $0.0000 | $0.00 |
| Mar 2, 2026 | Fisher Daniel Mark | Group Head of HR & Comm. | F | 2,970 | $31.5900 | $93.82K |
| Mar 2, 2026 | Carreiro Gemma Elizabeth | Group General Counsel | A | 16,760 | $0.0000 | $0.00 |
| Mar 2, 2026 | Baker Alexander James | CEO, Hamilton Global Specialty | A | 14,245 | $0.0000 | $0.00 |
| Mar 2, 2026 | Levenson Jonathan B. | Group Treasurer | A | 7,070 | $0.0000 | $0.00 |
| Mar 2, 2026 | Levenson Jonathan B. | Group Treasurer | F | 2,512 | $31.5900 | $79.35K |
| Mar 2, 2026 | Karrenbauer Raymond | Chief Information Officer | A | 8,428 | $0.0000 | $0.00 |
| Mar 2, 2026 | Deegan Brian John | Group Chief Accounting Officer | A | 11,260 | $0.0000 | $0.00 |
| Mar 2, 2026 | Howie Craig | Chief Financial Officer | A | 32,472 | $0.0000 | $0.00 |
| Mar 2, 2026 | Howie Craig | Chief Financial Officer | F | 11,729 | $31.5900 | $370.52K |
| Mar 2, 2026 | Kuchma Anita Breslin | CEO, Hamilton Select | A | 9,198 | $0.0000 | $0.00 |
| Mar 2, 2026 | Kuchma Anita Breslin | CEO, Hamilton Select | F | 2,198 | $31.5900 | $69.43K |
| Mar 2, 2026 | Duffin Timothy James | Chief Underwriting Officer | A | 12,832 | $0.0000 | $0.00 |
| Mar 2, 2026 | Daws Adrian Joseph | CEO, Hamilton Re | A | 20,000 | $0.0000 | $0.00 |
| Mar 2, 2026 | Daws Adrian Joseph | CEO, Hamilton Re | F | 4,760 | $31.5900 | $150.37K |
| Mar 2, 2026 | Buckley Russell John | Group Chief Risk Officer | A | 6,874 | $0.0000 | $0.00 |
| Mar 2, 2026 | Daws Adrian Joseph | CEO, Hamilton Re | A | 20,000 | $0.0000 | $0.00 |
| Mar 2, 2026 | Daws Adrian Joseph | CEO, Hamilton Re | F | 4,699 | $31.5900 | $148.44K |
| Feb 24, 2026 | Albo Giuseppina | Chief Executive Officer | F | 120,809 | $30.5500 | $3.69M |
| Feb 24, 2026 | Albo Giuseppina | Chief Executive Officer | A | 236,880 | $0.0000 | $0.00 |
| Feb 24, 2026 | Daws Adrian Joseph | CEO, Hamilton Re | F | 16,931 | $30.5500 | $517.24K |
| Feb 24, 2026 | Daws Adrian Joseph | CEO, Hamilton Re | A | 40,874 | $0.0000 | $0.00 |
| Feb 24, 2026 | Baker Alexander James | CEO, Hamilton Global Specialty | F | 12,394 | $30.5500 | $378.64K |
| Feb 24, 2026 | Baker Alexander James | CEO, Hamilton Global Specialty | A | 26,370 | $0.0000 | $0.00 |
| Feb 24, 2026 | Fisher Daniel Mark | Group Head of HR & Comm. | F | 8,594 | $30.5500 | $262.55K |
| Feb 24, 2026 | Fisher Daniel Mark | Group Head of HR & Comm. | A | 18,284 | $0.0000 | $0.00 |
| Feb 24, 2026 | Carreiro Gemma Elizabeth | Group General Counsel | A | 22,448 | $0.0000 | $0.00 |
| Feb 24, 2026 | Howie Craig | Chief Financial Officer | F | 34,374 | $30.5500 | $1.05M |
| Feb 24, 2026 | Howie Craig | Chief Financial Officer | A | 87,464 | $0.0000 | $0.00 |
| Feb 24, 2026 | Kuchma Anita Breslin | CEO, Hamilton Select | F | 7,286 | $30.5500 | $222.59K |
| Feb 24, 2026 | Kuchma Anita Breslin | CEO, Hamilton Select | A | 20,408 | $0.0000 | $0.00 |