HG

SEC source: 0001140361-24-012053 · form4.xml · derivative · entry 2

Kuchma Anita Breslin · CIK 0001999605 · CEO, Hamilton Select

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,069

Underlying: Class B Common Shares · 12,069 shares

Expires not disclosed

F2 · derivative.exercise_price: On March 5, 2024 the reporting person was granted 12,069 performance stock units ('PSUs') that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F2 · derivative.exercise_date: On March 5, 2024 the reporting person was granted 12,069 performance stock units ('PSUs') that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F2 · derivative.expiration_date: On March 5, 2024 the reporting person was granted 12,069 performance stock units ('PSUs') that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

SEC source: 0001140361-24-012053 · form4.xml · nonDerivative · entry 1

Kuchma Anita Breslin · CIK 0001999605 · CEO, Hamilton Select

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,794

F1 · price: On March 5, 2024, the reporting person was granted 12,069 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share.

SEC source: 0001140361-24-012060 · form4.xml · derivative · entry 5

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 123,276

Underlying: Class B Common Shares · 123,276 shares

Expires not disclosed

F3 · derivative.exercise_price: On March 5, 2024, the reporting person was granted 123,276 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.exercise_date: On March 5, 2024, the reporting person was granted 123,276 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.expiration_date: On March 5, 2024, the reporting person was granted 123,276 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

SEC source: 0001140361-24-012060 · form4.xml · derivative · entry 4

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 23,480 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: On March 30, 2021, the reporting person was granted 73,605 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 73,605 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 73,605 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012060 · form4.xml · nonDerivative · entry 2

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 614,256

F2 · price: On March 5, 2024, the reporting person was granted 123,276 restricted stock units ("RSUs") that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

SEC source: 0001140361-24-012060 · form4.xml · nonDerivative · entry 1

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 490,980

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On March 30, 2021, the reporting person was granted 73,605 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012057 · form4.xml · derivative · entry 4

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,793

Underlying: Class B Common Shares · 13,793 shares

Expires not disclosed

F3 · derivative.exercise_price: On March 5, 2024 the reporting person was granted 13,793 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.exercise_date: On March 5, 2024 the reporting person was granted 13,793 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.expiration_date: On March 5, 2024 the reporting person was granted 13,793 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

SEC source: 0001140361-24-012057 · form4.xml · derivative · entry 3

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 2,673 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: On March 30, 2021, the reporting person was granted 8,380 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 8,380 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 8,380 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012057 · form4.xml · nonDerivative · entry 2

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 55,264

F2 · price: On March 5, 2024, the reporting person was granted 13,793 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

SEC source: 0001140361-24-012057 · form4.xml · nonDerivative · entry 1

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 41,471

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On March 30, 2021, the reporting person was granted 8,380 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012054 · form4.xml · nonDerivative · entry 1

Deegan Brian John · CIK 0001999604 · Group Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,957

F1 · price: On March 5, 2024, the reporting person was granted 17,379 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share.

SEC source: 0001140361-24-012059 · form4.xml · derivative · entry 4

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,552

Underlying: Class B Common Shares · 32,552 shares

Expires not disclosed

F3 · derivative.exercise_price: On March 5, 2024 the reporting person was granted 32,552 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.exercise_date: On March 5, 2024 the reporting person was granted 32,552 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.expiration_date: On March 5, 2024 the reporting person was granted 32,552 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

SEC source: 0001140361-24-012059 · form4.xml · derivative · entry 3

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 6,020 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: On March 30, 2021, the reporting person was granted 18,873 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 18,873 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 18,873 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012059 · form4.xml · nonDerivative · entry 2

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 123,394

F2 · price: On March 5, 2024, the reporting person was granted 32,552 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

SEC source: 0001140361-24-012059 · form4.xml · nonDerivative · entry 1

Thomas Megan Jane · CIK 0001999553 · CEO, Hamilton Re

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 90,842

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On March 30, 2021, the reporting person was granted 18,873 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012055 · form4.xml · derivative · entry 2

Howie Craig · CIK 0001549925 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 47,586

Underlying: Class B Common Shares · 47,586 shares

Expires not disclosed

F2 · derivative.exercise_price: On March 5, 2024 the reporting person was granted 47,586 performance stock units ("PSUs") that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F2 · derivative.exercise_date: On March 5, 2024 the reporting person was granted 47,586 performance stock units ("PSUs") that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F2 · derivative.expiration_date: On March 5, 2024 the reporting person was granted 47,586 performance stock units ("PSUs") that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

SEC source: 0001140361-24-012055 · form4.xml · nonDerivative · entry 1

Howie Craig · CIK 0001549925 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 67,520

F1 · price: On March 5, 2024, the reporting person was granted 47,586 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

SEC source: 0001140361-24-012061 · form4.xml · derivative · entry 4

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,052

Underlying: Class B Common Shares · 9,052 shares

Expires not disclosed

F3 · derivative.exercise_price: On March 5, 2024 the reporting person was granted 9,052 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.exercise_date: On March 5, 2024 the reporting person was granted 9,052 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.expiration_date: On March 5, 2024 the reporting person was granted 9,052 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

SEC source: 0001140361-24-012061 · form4.xml · derivative · entry 3

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 2,167 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: On March 30, 2021, the reporting person was granted 6,794 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 6,794 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 6,794 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012061 · form4.xml · nonDerivative · entry 2

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 31,760

F2 · price: On March 5, 2024, the reporting person was granted 9,052 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

SEC source: 0001140361-24-012061 · form4.xml · nonDerivative · entry 1

Krishnamoorthy Venkatanarayanan · CIK 0001999843 · Group CTO and Group CDO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,708

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On March 30, 2021, the reporting person was granted 6,794 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012052 · form4.xml · derivative · entry 4

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,245

Underlying: Class B Common Shares · 25,245 shares

Expires not disclosed

F3 · derivative.exercise_price: On March 5, 2024 the reporting person was granted 25,245 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.exercise_date: On March 5, 2024 the reporting person was granted 25,245 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F3 · derivative.expiration_date: On March 5, 2024 the reporting person was granted 25,245 PSUs that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

SEC source: 0001140361-24-012052 · form4.xml · derivative · entry 3

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 25,245 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: On March 30, 2021, the reporting person was granted 14,445 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 14,445 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

F1 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 14,445 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012052 · form4.xml · nonDerivative · entry 2

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 115,757

F2 · shares: On March 5, 2024, the reporting person was granted 25,245 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

F2 · price: On March 5, 2024, the reporting person was granted 25,245 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

SEC source: 0001140361-24-012052 · form4.xml · nonDerivative · entry 1

Daws Adrian Joseph · CIK 0001999704 · CEO, Hamilton Global Specialty

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 90,512

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: On March 30, 2021, the reporting person was granted 14,445 performance stock units ("PSUs") that could be earned based on our annualized underwriting return on capital for the 3-year performance period ending on December 31, 2023. Each PSU represented a contingent right to receive one Class B common share.

SEC source: 0001140361-24-012051 · form4.xml · derivative · entry 2

Baker Alexander James · CIK 0001999736 · Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,778

Underlying: Class B Common Shares · 15,778 shares

Expires not disclosed

F2 · derivative.exercise_price: On March 5, 2024 the reporting person was granted 15,778 performance stock units ('PSUs') that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F2 · derivative.exercise_date: On March 5, 2024 the reporting person was granted 15,778 performance stock units ('PSUs') that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

F2 · derivative.expiration_date: On March 5, 2024 the reporting person was granted 15,778 performance stock units ('PSUs') that are earned based on two equally-weighted performance measures: (i) Return on Equity and (ii) Book Value per Share growth, both measured on an absolute basis, for the 3-year performance period ending on December 31, 2026. Each PSU represents a contingent right to receive one Class B common share. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of the performance target during the performance period.

SEC source: 0001140361-24-012051 · form4.xml · nonDerivative · entry 1

Baker Alexander James · CIK 0001999736 · Chief Risk Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 58,128

F1 · shares: On March 5, 2024, the reporting person was granted 15,778 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

F1 · price: On March 5, 2024, the reporting person was granted 15,778 restricted stock units ('RSUs') that vest one-third per year on January 1, 2025, 2026 and 2027, respectively. Each RSU represents the right to receive one Class B common share. The number reported here reflects the RSUs outstanding subject to future vesting.

SEC source: 0001140361-24-011537 · form4.xml · nonDerivative · entry 1

FRADIN RUSSELL P · CIK 0001140933 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 178,671

F1 · shares: The number of shares delivered to the reporting person relating to a portion of the compensation paid to the reporting person in the amount of $47,500 for service on the Board of Directors of the issuer from July 1, 2023 through December 31, 2023.

F2 · price: The value of the shares at the end of the period of service by the reporting person which was used to determine the number of shares to be delivered to the reporting person.

SEC source: 0001140361-24-011538 · form4.xml · nonDerivative · entry 1

Pacala Stephen Wilson · CIK 0001999582 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,876

F1 · shares: The number of shares delivered to the reporting person relating to a portion of the compensation paid to the reporting person in the amount of $37,500 for service on the Board of Directors of the issuer from July 1, 2023 through December 31, 2023.

F2 · price: The value of the shares at the end of the period of service by the reporting person which was used to determine the number of shares to be delivered to the reporting person.

SEC source: 0001140361-24-011532 · form4.xml · derivative · entry 4

Bernhard Keith Donald · CIK 0001999608 · Group Chief Audit Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,595

Underlying: Class B Common Shares · 3,298 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 9,893 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F4 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 9,893 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011532 · form4.xml · derivative · entry 3

Bernhard Keith Donald · CIK 0001999608 · Group Chief Audit Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,008

Underlying: Class B Common Shares · 3,009 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F3 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 9,026 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F3 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 9,026 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011532 · form4.xml · derivative · entry 2

Bernhard Keith Donald · CIK 0001999608 · Group Chief Audit Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 3,357 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F2 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 10,073 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

F2 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 10,073 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011532 · form4.xml · nonDerivative · entry 1

Bernhard Keith Donald · CIK 0001999608 · Group Chief Audit Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 76,798

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011525 · form4.xml · derivative · entry 4

Cundliffe Chad Allan · CIK 0001999638 · Group Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,762

Underlying: Class B Common Shares · 6,381 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 19,143 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F4 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 19,143 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011525 · form4.xml · derivative · entry 3

Cundliffe Chad Allan · CIK 0001999638 · Group Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,726

Underlying: Class B Common Shares · 5,726 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F3 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 17,179 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F3 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 17,179 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011525 · form4.xml · derivative · entry 2

Cundliffe Chad Allan · CIK 0001999638 · Group Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 6,208 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F2 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 18,624 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

F2 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 18,624 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011525 · form4.xml · nonDerivative · entry 1

Cundliffe Chad Allan · CIK 0001999638 · Group Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 104,132

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011528 · form4.xml · derivative · entry 5

Fisher Daniel Mark · CIK 0001999653 · Group Head of HR & Comm.

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,095

Underlying: Class B Common Shares · 3,047 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: RSUs convert into Class B Common Shares on a one-for-one basis.

F6 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 9,142 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F6 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 9,142 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011528 · form4.xml · derivative · entry 4

Fisher Daniel Mark · CIK 0001999653 · Group Head of HR & Comm.

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,661

Underlying: Class B Common Shares · 2,660 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: RSUs convert into Class B Common Shares on a one-for-one basis.

F5 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 7,982 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F5 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 7,982 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011528 · form4.xml · derivative · entry 3

Fisher Daniel Mark · CIK 0001999653 · Group Head of HR & Comm.

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 2,579 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: RSUs convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 7,739 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

F4 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 7,739 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011528 · form4.xml · nonDerivative · entry 1

Fisher Daniel Mark · CIK 0001999653 · Group Head of HR & Comm.

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 29,064

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · price: RSUs convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011522 · form4.xml · derivative · entry 4

Kuchma Anita Breslin · CIK 0001999605 · CEO, Hamilton Select

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,803

Underlying: Class B Common Shares · 3,401 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: RSUs convert into Class B Common Shares on a one-for-one basis.

F5 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 10,204 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F5 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 10,204 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011522 · form4.xml · derivative · entry 3

Kuchma Anita Breslin · CIK 0001999605 · CEO, Hamilton Select

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,687

Underlying: Class B Common Shares · 1,687 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: RSUs convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 5,601 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F4 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 5,601 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011522 · form4.xml · nonDerivative · entry 1

Kuchma Anita Breslin · CIK 0001999605 · CEO, Hamilton Select

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,393

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · price: RSUs convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011535 · form4.xml · derivative · entry 6

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 78,960

Underlying: Class B Common Shares · 39,480 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: RSUs convert into Class B Common Shares on a one-for-one basis.

F6 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 9,566 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F6 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 9,566 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011535 · form4.xml · derivative · entry 5

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 29,240

Underlying: Class B Common Shares · 29,239 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: RSUs convert into Class B Common Shares on a one-for-one basis.

F5 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 7,287 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F5 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 7,287 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

SEC source: 0001140361-24-011535 · form4.xml · derivative · entry 4

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Shares · 24,535 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: RSUs convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 30, 2021, the reporting person was granted 6,794 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

F4 · derivative.expiration_date: On March 30, 2021, the reporting person was granted 6,794 RSUs vesting in equal installments on each of January 1, 2022, 2023 and 2024.

SEC source: 0001140361-24-011535 · form4.xml · nonDerivative · entry 1

Albo Giuseppina · CIK 0001999598 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 515,703

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · price: RSUs convert into Class B Common Shares on a one-for-one basis.

SEC source: 0001140361-24-011529 · form4.xml · derivative · entry 4

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,482

Underlying: Class B Common Shares · 3,742 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F4 · derivative.exercise_date: On March 10, 2023, the reporting person was granted 11,224 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

F4 · derivative.expiration_date: On March 10, 2023, the reporting person was granted 11,224 RSUs vesting in equal installments on each of January 1, 2024, 2025 and 2026.

SEC source: 0001140361-24-011529 · form4.xml · derivative · entry 3

Carreiro Gemma Elizabeth · CIK 0001999708 · Group General Counsel

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,912

Underlying: Class B Common Shares · 2,913 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Restricted stock units ("RSUs") convert into Class B Common Shares on a one-for-one basis.

F3 · derivative.exercise_date: On February 11, 2022, the reporting person was granted 8,738 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.

F3 · derivative.expiration_date: On February 11, 2022, the reporting person was granted 8,738 RSUs vesting in equal installments on each of January 1, 2023, 2024 and 2025.