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Fair Value Measurements - Financial Assets Measured on Recurring Basis (Details) - USD ($)
$ in Millions
Dec. 31, 2022
Dec. 31, 2021
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Catastrophe Bonds, Fair Value Disclosure $ 5.1 $ 5.3
Derivatives at fair value 56.2 12.9
Recurring    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Total 6,100.9 6,512.6
Recurring | Derivatives at fair value | Foreign exchange contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Derivatives at fair value 56.2 12.9
Recurring | Liabilities under derivative contracts | Foreign exchange contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value (3.2) (13.3)
Recurring | Liabilities under derivative contracts | Loss Portfolio Transfer    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value (31.7)  
Recurring | Total fixed income securities — Available for sale | Non-agency commercial mortgage-backed securities    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 5.6  
Recurring | Fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 3,788.6 4,881.6
Recurring | Short-term investments    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 52.0 10.1
Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,475.5 1,157.5
Privately-held Investments, at fair value 533.0 307.1
Catastrophe Bonds, Fair Value Disclosure 2.9 3.4
Recurring | Short-term investments trading at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 6.3 2.0
Recurring | Real estate fund    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 221.3 151.3
Recurring | Level 1    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Total 1,428.7 1,384.5
Recurring | Level 1 | Derivatives at fair value | Foreign exchange contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Derivatives at fair value 0.0 0.0
Recurring | Level 1 | Liabilities under derivative contracts | Foreign exchange contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value 0.0 0.0
Recurring | Level 1 | Liabilities under derivative contracts | Loss Portfolio Transfer    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value 0.0  
Recurring | Level 1 | Total fixed income securities — Available for sale | Non-agency commercial mortgage-backed securities    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0  
Recurring | Level 1 | Fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,098.3 1,248.7
Recurring | Level 1 | Short-term investments    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 51.9 6.5
Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 272.2 128.2
Privately-held Investments, at fair value 0.0 0.0
Catastrophe Bonds, Fair Value Disclosure 0.0 0.0
Recurring | Level 1 | Short-term investments trading at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 6.3 1.1
Recurring | Level 1 | Real estate fund    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 2    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Total 3,949.6 4,669.7
Recurring | Level 2 | Derivatives at fair value | Foreign exchange contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Derivatives at fair value 56.2 12.9
Recurring | Level 2 | Liabilities under derivative contracts | Foreign exchange contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value (3.2) (13.3)
Recurring | Level 2 | Liabilities under derivative contracts | Loss Portfolio Transfer    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value 0.0  
Recurring | Level 2 | Total fixed income securities — Available for sale | Non-agency commercial mortgage-backed securities    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 5.6  
Recurring | Level 2 | Fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 2,690.3 3,632.9
Recurring | Level 2 | Short-term investments    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.1 3.6
Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,203.3 1,029.3
Privately-held Investments, at fair value 0.0 0.0
Catastrophe Bonds, Fair Value Disclosure 2.9 3.4
Recurring | Level 2 | Short-term investments trading at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.9
Recurring | Level 2 | Real estate fund    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Total 501.3 307.1
Recurring | Level 3 | Derivatives at fair value | Foreign exchange contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Derivatives at fair value 0.0 0.0
Recurring | Level 3 | Liabilities under derivative contracts | Foreign exchange contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value 0.0 0.0
Recurring | Level 3 | Liabilities under derivative contracts | Loss Portfolio Transfer    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value (31.7)  
Recurring | Level 3 | Total fixed income securities — Available for sale | Non-agency commercial mortgage-backed securities    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0  
Recurring | Level 3 | Fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Short-term investments    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Privately-held Investments, at fair value 533.0 307.1
Catastrophe Bonds, Fair Value Disclosure 0.0 0.0
Recurring | Level 3 | Short-term investments trading at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Real estate fund    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
U.S. government | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 953.0 1,084.3
U.S. government | Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 261.6 116.3
U.S. government | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 953.0 1,084.3
U.S. government | Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 261.6 116.3
U.S. government | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
U.S. government | Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
U.S. government | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
U.S. government | Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
U.S. agency | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 8.8 21.5
U.S. agency | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
U.S. agency | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 8.8 21.5
U.S. agency | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Municipal | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 149.5 82.6
Municipal | Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 3.6 4.0
Municipal | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Municipal | Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Municipal | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 149.5 82.6
Municipal | Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 3.6 4.0
Municipal | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Municipal | Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Corporate | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,845.0 2,208.3
Corporate | Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 162.1 96.8
Corporate | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Corporate | Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Corporate | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,845.0 2,208.3
Corporate | Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 162.1 96.8
Corporate | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Corporate | Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Non-U.S. government-backed corporate | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 110.4 136.8
Non-U.S. government-backed corporate | Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 11.6 13.1
Non-U.S. government-backed corporate | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Non-U.S. government-backed corporate | Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Non-U.S. government-backed corporate | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 110.4 136.8
Non-U.S. government-backed corporate | Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 11.6 13.1
Non-U.S. government-backed corporate | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Non-U.S. government-backed corporate | Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Non-U.S government | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 213.6 250.7
Non-U.S government | Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 30.4 34.5
Non-U.S government | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 145.3 164.4
Non-U.S government | Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 10.6 11.9
Non-U.S government | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 68.3 86.3
Non-U.S government | Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 19.8 22.6
Non-U.S government | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Non-U.S government | Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Asset-backed | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.5
Asset-backed | Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 896.5 785.7
Asset-backed | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Asset-backed | Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Asset-backed | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.5
Asset-backed | Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 896.5 785.7
Asset-backed | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Asset-backed | Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Non-agency commercial mortgage-backed securities | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value   6.9
Non-agency commercial mortgage-backed securities | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value   0.0
Non-agency commercial mortgage-backed securities | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value   6.9
Non-agency commercial mortgage-backed securities | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value   0.0
Agency mortgage-backed | Recurring | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 502.7 1,090.0
Agency mortgage-backed | Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 21.4 30.2
Agency mortgage-backed | Recurring | Level 1 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Agency mortgage-backed | Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Agency mortgage-backed | Recurring | Level 2 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 502.7 1,090.0
Agency mortgage-backed | Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 21.4 30.2
Agency mortgage-backed | Recurring | Level 3 | Total fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Agency mortgage-backed | Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
High yield loans | Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 88.3 76.9
High yield loans | Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
High yield loans | Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 88.3 76.9
High yield loans | Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value $ 0.0 $ 0.0