HG's three largest insider shareholders as of September 09, 2026 are Investments, Lp Hamilton (TenPercentOwner, 4.53Mn shares), Investments, Lp Hamilton (TenPercentOwner, 4.53Mn shares), Investments, Lp Hamilton (TenPercentOwner, 4.53Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Investments, Lp Hamilton | TenPercentOwner | 4,330,821 | 200,000 | 4,530,821 | 55.2% | 16 Nov, 2023 |
| 2 | Giuseppina Albo | Chief Executive Officer | 985,815 | 0 | 985,815 | 12.0% | 17 Aug, 2026 |
| 3 | David A Brown | Director | 0 | 400,000 | 400,000 | 4.9% | 08 Sep, 2026 |
| 4 | Craig Howie | Chief Financial Officer | 282,372 | 0 | 282,372 | 3.4% | 04 Mar, 2026 |
| 5 | Timothy James Duffin | Chief Underwriting Officer | 251,959 | 0 | 251,959 | 3.1% | 04 Mar, 2026 |
| 6 | Adrian Joseph Daws | Ceo, Hamilton Re | 212,547 | 0 | 212,547 | 2.6% | 07 May, 2026 |
| 7 | Gemma Elizabeth Carreiro | Group General Counsel | 190,615 | 0 | 190,615 | 2.3% | 04 Mar, 2026 |
| 8 | Russell P Fradin | Director | 178,671 | 0 | 178,671 | 2.2% | 05 Mar, 2024 |
| 9 | Doreen Pauline Elizabeth Richards | Director | 113,054 | 0 | 113,054 | 1.4% | 05 Mar, 2024 |
| 10 | Alexander James Baker | Ceo, Hamilton Global Specialty | 110,291 | 0 | 110,291 | 1.3% | 04 Mar, 2026 |
| 11 | Daniel Mark Fisher | Group Head Of Hr Comm. | 106,265 | 0 | 106,265 | 1.3% | 04 Mar, 2026 |
| 12 | Megan Jane Graves | Ceo, Hamilton Re | 104,674 | 0 | 104,674 | 1.3% | 14 Aug, 2025 |
| 13 | Chad Allan Cundliffe | Group Treasurer | 104,132 | 0 | 104,132 | 1.3% | 05 Mar, 2024 |
| 14 | Anita Breslin Kuchma | Ceo, Hamilton Select | 89,278 | 0 | 89,278 | 1.1% | 04 Mar, 2026 |
| 15 | Brian John Deegan | Group Chief Accounting Officer | 71,347 | 0 | 71,347 | 0.9% | 07 May, 2026 |
| 16 | Marvin Pestcoe | Director | 68,548 | 0 | 68,548 | 0.8% | 07 May, 2026 |
| 17 | Venkatanarayanan Krishnamoorthy | Group Cto And Group Cdo | 64,512 | 0 | 64,512 | 0.8% | 18 Aug, 2025 |
| 18 | Keith Donald Bernhard | Group Chief Audit Officer | 53,893 | 0 | 53,893 | 0.7% | 08 Sep, 2025 |
| 19 | William C Freda | Director | 47,194 | 0 | 47,194 | 0.6% | 05 Mar, 2024 |
| 20 | Stephen Wilson Pacala | Director | 40,876 | 0 | 40,876 | 0.5% | 05 Mar, 2024 |
| 21 | Jonathan B. Levenson | Group Treasurer | 39,629 | 0 | 39,629 | 0.5% | 15 May, 2026 |
| 22 | John J Gauthier | Director | 32,012 | 0 | 32,012 | 0.4% | 07 May, 2026 |
| 23 | Therese M Vaughan | Director | 25,821 | 0 | 25,821 | 0.3% | 07 May, 2026 |
| 24 | Everard Barclay Simmons | Director | 22,952 | 0 | 22,952 | 0.3% | 07 May, 2026 |
| 25 | Anu Karna | Director | 22,012 | 0 | 22,012 | 0.3% | 07 May, 2026 |
| 26 | Alan Neil Patterson | Director | 21,071 | 0 | 21,071 | 0.3% | 07 May, 2026 |
| 27 | David Priebe | Director | 12,116 | 0 | 12,116 | 0.1% | 07 May, 2026 |
| 28 | Karen Ann Green | Director | 8,738 | 0 | 8,738 | 0.1% | 07 May, 2026 |
| 29 | Raymond Karrenbauer | Chief Information Officer | 8,428 | 0 | 8,428 | 0.1% | 04 Mar, 2026 |
| 30 | Russell John Buckley | Group Chief Risk Officer | 6,874 | 0 | 6,874 | 0.1% | 04 Mar, 2026 |
| 31 | Peter W Wilson | Director | 4,929 | 0 | 4,929 | 0.1% | 07 May, 2026 |
| 32 | Bradley E Cooper | Director | 99 | 0 | 99 | 0.0% | 17 Apr, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 03 Sep, 2026 | David A Brown | Director | Disposed S | 50,000 | $36.12 | $1.81Mn | 400,000 | Indirect |
| 13 Aug, 2026 | Giuseppina Albo | Chief Executive Officer | Disposed G | 100,430 | $0.00 | $0 | 1,086,245 | Direct |
| 13 Aug, 2026 | Giuseppina Albo | Chief Executive Officer | Disposed G | 100,430 | $0.00 | $0 | 985,815 | Direct |
| 13 Aug, 2026 | Giuseppina Albo | Chief Executive Officer | Acquired G | 100,430 | $0.00 | $0 | 100,430 | Indirect |
| 13 Aug, 2026 | Giuseppina Albo | Chief Executive Officer | Disposed G | 100,430 | $0.00 | $0 | 0 | Indirect |
| 18 May, 2026 | David A Brown | Director | Disposed S | 37,300 | $32.16 | $1.20Mn | 450,000 | Indirect |
| 15 May, 2026 | David A Brown | Director | Disposed S | 12,700 | $31.82 | $404.12K | 487,300 | Indirect |
| 13 May, 2026 | Jonathan B. Levenson | Group Treasurer | Disposed S | 6,075 | $30.61 | $185.96K | 39,629 | Direct |
| 08 May, 2026 | Jonathan B. Levenson | Group Treasurer | Disposed S | 3,030 | $30.67 | $92.93K | 45,704 | Direct |
| 05 May, 2026 | Everard Barclay Simmons | Director | Acquired A | 4,929 | $0.00 | $0 | 22,952 | Direct |
| 05 May, 2026 | Therese M Vaughan | Director | Acquired A | 4,929 | $0.00 | $0 | 25,821 | Direct |
| 05 May, 2026 | Marvin Pestcoe | Director | Acquired A | 4,929 | $0.00 | $0 | 68,548 | Direct |
| 05 May, 2026 | John J Gauthier | Director | Acquired A | 4,929 | $0.00 | $0 | 32,012 | Direct |
| 05 May, 2026 | Alan Neil Patterson | Director | Acquired A | 4,929 | $0.00 | $0 | 21,071 | Direct |
| 05 May, 2026 | Brian John Deegan | Group Chief Accounting Officer | Disposed S | 11,000 | $30.69 | $337.64K | 71,347 | Direct |
| 02 Mar, 2026 | Adrian Joseph Daws | Ceo, Hamilton Re | Disposed F | 4,699 | $31.59 | $148.44K | 192,547 | Direct |
| 05 May, 2026 | Peter W Wilson | Director | Acquired A | 4,929 | $0.00 | $0 | 4,929 | Direct |
| 05 May, 2026 | David Priebe | Director | Acquired A | 4,929 | $0.00 | $0 | 12,116 | Direct |
| 05 May, 2026 | David A Brown | Director | Acquired A | 4,929 | $0.00 | $0 | 110,308 | Direct |
| 05 May, 2026 | Anu Karna | Director | Acquired A | 4,929 | $0.00 | $0 | 22,012 | Direct |