HG insider transactions

Director Brown David A sold $1,199,654 worth of Class B Common Shares (37,300 units at $32.16) (SEC Form 4)

Director Brown David A sold $404,117 worth of Class B Common Shares (12,700 units at $31.82) (SEC Form 4)

Group Treasurer Levenson Jonathan B. sold $185,956 worth of Class B Common Shares (6,075 units at $30.61), decreasing direct ownership by 13% to 39,629 units (SEC Form 4)

Group Treasurer Levenson Jonathan B. sold $92,930 worth of Class B Common Shares (3,030 units at $30.67), decreasing direct ownership by 6% to 45,704 units (SEC Form 4)

Director Vaughan Therese M was granted 4,929 units of Class B Common Shares, increasing direct ownership by 24% to 25,821 units (SEC Form 4)

Group Chief Accounting Officer Deegan Brian John sold $337,644 worth of Class B Common Shares (11,000 units at $30.69), decreasing direct ownership by 13% to 71,347 units (SEC Form 4)

Director Patterson Alan Neil was granted 4,929 units of Class B Common Shares, increasing direct ownership by 31% to 21,071 units (SEC Form 4)

Director Pestcoe Marvin was granted 4,929 units of Class B Common Shares, increasing direct ownership by 8% to 68,548 units (SEC Form 4)

Director Simmons Everard Barclay was granted 4,929 units of Class B Common Shares, increasing direct ownership by 27% to 22,952 units (SEC Form 4)

Director Brown David A was granted 4,929 units of Class B Common Shares, increasing direct ownership by 5% to 110,308 units (SEC Form 4)

Director Karna Anu was granted 4,929 units of Class B Common Shares, increasing direct ownership by 29% to 22,012 units (SEC Form 4)

Director Wilson Peter W was granted 4,929 units of Class B Common Shares (SEC Form 4)

Director Priebe David was granted 4,929 units of Class B Common Shares, increasing direct ownership by 69% to 12,116 units (SEC Form 4)

Director Gauthier John J was granted 4,929 units of Class B Common Shares, increasing direct ownership by 18% to 32,012 units (SEC Form 4)

Director Green Karen Ann was granted 4,929 units of Class B Common Shares and covered exercise/tax liability with 3,378 units of Class B Common Shares, increasing direct ownership by 22% to 8,738 units (SEC Form 4) (for withholding tax)

Amendment: CEO, Hamilton Re Daws Adrian Joseph covered exercise/tax liability with 4,699 units of Class B Common Shares and was granted 20,000 units of Class B Common Shares, increasing direct ownership by 8% to 212,547 units (SEC Form 4) (tax liability)

SEC Form 3 filed by new insider Wilson Peter W

SEC Form 4 filed by Cooper Bradley E

CEO, Hamilton Re Daws Adrian Joseph was granted 20,000 units of Class B Common Shares and covered exercise/tax liability with 4,760 units of Class B Common Shares, increasing direct ownership by 8% to 212,486 units (SEC Form 4)

Group Chief Risk Officer Buckley Russell John was granted 6,874 units of Class B Common Shares (SEC Form 4)

Chief Underwriting Officer Duffin Timothy James was granted 12,832 units of Class B Common Shares, increasing direct ownership by 5% to 251,959 units (SEC Form 4)

Group Chief Accounting Officer Deegan Brian John was granted 11,260 units of Class B Common Shares, increasing direct ownership by 16% to 82,347 units (SEC Form 4)

Chief Financial Officer Howie Craig covered exercise/tax liability with 11,729 units of Class B Common Shares and was granted 32,472 units of Class B Common Shares, increasing direct ownership by 8% to 282,372 units (SEC Form 4)

CEO, Hamilton Select Kuchma Anita Breslin covered exercise/tax liability with 2,198 units of Class B Common Shares and was granted 9,198 units of Class B Common Shares, increasing direct ownership by 9% to 89,278 units (SEC Form 4)

Chief Information Officer Karrenbauer Raymond was granted 8,428 units of Class B Common Shares (SEC Form 4)

CEO, Hamilton Global Specialty Baker Alexander James was granted 14,245 units of Class B Common Shares, increasing direct ownership by 15% to 110,291 units (SEC Form 4)

Group Treasurer Levenson Jonathan B. was granted 7,070 units of Class B Common Shares and covered exercise/tax liability with 2,512 units of Class B Common Shares, increasing direct ownership by 10% to 48,734 units (SEC Form 4)

Group General Counsel Carreiro Gemma Elizabeth was granted 16,760 units of Class B Common Shares, increasing direct ownership by 10% to 190,615 units (SEC Form 4)

Group Head of HR & Comm. Fisher Daniel Mark covered exercise/tax liability with 2,970 units of Class B Common Shares and was granted 10,882 units of Class B Common Shares, increasing direct ownership by 8% to 106,265 units (SEC Form 4)

Chief Executive Officer Albo Giuseppina covered exercise/tax liability with 37,818 units of Class B Common Shares and was granted 81,015 units of Class B Common Shares, increasing direct ownership by 4% to 1,186,675 units (SEC Form 4)

CEO, Hamilton Select Kuchma Anita Breslin covered exercise/tax liability with 7,286 units of Class B Common Shares and was granted 20,408 units of Class B Common Shares, increasing direct ownership by 19% to 82,278 units (SEC Form 4)

Group General Counsel Carreiro Gemma Elizabeth was granted 22,448 units of Class B Common Shares, increasing direct ownership by 15% to 173,855 units (SEC Form 4)

Chief Financial Officer Howie Craig was granted 87,464 units of Class B Common Shares and covered exercise/tax liability with 34,374 units of Class B Common Shares, increasing direct ownership by 25% to 261,629 units (SEC Form 4)

Group Head of HR & Comm. Fisher Daniel Mark covered exercise/tax liability with 8,594 units of Class B Common Shares and was granted 18,284 units of Class B Common Shares, increasing direct ownership by 11% to 98,353 units (SEC Form 4)

CEO, Hamilton Global Specialty Baker Alexander James was granted 26,370 units of Class B Common Shares and covered exercise/tax liability with 12,394 units of Class B Common Shares, increasing direct ownership by 17% to 96,046 units (SEC Form 4)

SEC Form 3 filed by new insider Roston Marc Nathan

CEO, Hamilton Re Daws Adrian Joseph was granted 40,874 units of Class B Common Shares and covered exercise/tax liability with 16,931 units of Class B Common Shares, increasing direct ownership by 14% to 197,246 units (SEC Form 4)

Chief Executive Officer Albo Giuseppina was granted 236,880 units of Class B Common Shares and covered exercise/tax liability with 120,809 units of Class B Common Shares, increasing direct ownership by 11% to 1,143,478 units (SEC Form 4)

Group Treasurer Levenson Jonathan B. covered exercise/tax liability with 1,689 units of Class B Common Shares, decreasing direct ownership by 4% to 44,176 units (SEC Form 4)

Chief Executive Officer Albo Giuseppina covered exercise/tax liability with 19,200 units of Class B Common Shares, decreasing direct ownership by 2% to 1,027,407 units (SEC Form 4)

CEO, Hamilton Select Kuchma Anita Breslin covered exercise/tax liability with 1,118 units of Class B Common Shares, decreasing direct ownership by 2% to 69,156 units (SEC Form 4)

CEO, Hamilton Global Specialty Baker Alexander James covered exercise/tax liability with 2,066 units of Class B Common Shares, decreasing direct ownership by 2% to 82,070 units (SEC Form 4)

CEO, Hamilton Re Daws Adrian Joseph covered exercise/tax liability with 2,823 units of Class B Common Shares, decreasing direct ownership by 2% to 173,303 units (SEC Form 4)

Group Head of HR & Comm. Fisher Daniel Mark covered exercise/tax liability with 1,433 units of Class B Common Shares, decreasing direct ownership by 2% to 88,663 units (SEC Form 4)

Chief Financial Officer Howie Craig covered exercise/tax liability with 6,084 units of Class B Common Shares, decreasing direct ownership by 3% to 208,539 units (SEC Form 4)

New insider Duffin Timothy James claimed ownership of 239,127 units of Class B Common Shares (SEC Form 3)

CEO, Hamilton Global Specialty Baker Alexander James sold $480,638 worth of Class B Common Shares (18,350 units at $26.19), decreasing direct ownership by 18% to 84,136 units (SEC Form 4)

Chief Executive Officer Albo Giuseppina covered exercise/tax liability with 75,935 units of Class B Common Shares, decreasing direct ownership by 7% to 1,046,607 units (SEC Form 4)

Chief Financial Officer Howie Craig covered exercise/tax liability with 19,906 units of Class B Common Shares, decreasing direct ownership by 8% to 214,623 units (SEC Form 4)

Group Treasurer Levenson Jonathan B. covered exercise/tax liability with 2,577 units of Class B Common Shares, decreasing direct ownership by 5% to 45,865 units (SEC Form 4)

CEO, Hamilton Global Specialty Baker Alexander James covered exercise/tax liability with 13,852 units of Class B Common Shares, decreasing direct ownership by 12% to 102,486 units (SEC Form 4)

CEO, Hamilton Select Kuchma Anita Breslin covered exercise/tax liability with 10,492 units of Class B Common Shares, decreasing direct ownership by 13% to 70,274 units (SEC Form 4)

Group Head of HR & Comm. Fisher Daniel Mark covered exercise/tax liability with 13,852 units of Class B Common Shares, decreasing direct ownership by 13% to 90,096 units (SEC Form 4)

CEO, Hamilton Re Daws Adrian Joseph covered exercise/tax liability with 14,314 units of Class B Common Shares, decreasing direct ownership by 8% to 176,126 units (SEC Form 4)

SEC Form 3 filed by new insider Karrenbauer Raymond

SEC Form 3 filed by new insider Buckley Russell John

Group Chief Audit Officer Bernhard Keith Donald sold $1,145,414 worth of Class B Common Shares (47,000 units at $24.37), decreasing direct ownership by 47% to 53,893 units (SEC Form 4)

Group CTO and Group CDO Krishnamoorthy Venkatanarayanan sold $455,714 worth of Class B Common Shares (18,988 units at $24.00), decreasing direct ownership by 23% to 64,512 units (SEC Form 4)

Chief Risk Officer Baker Alexander James sold $142,724 worth of Class B Common Shares (6,000 units at $23.79), decreasing direct ownership by 5% to 116,338 units (SEC Form 4)

CEO, Hamilton Re Graves Megan Jane sold $1,187,340 worth of Class B Common Shares (50,000 units at $23.75), decreasing direct ownership by 32% to 104,674 units (SEC Form 4)