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Fair Value Measurements - Inputs Used (Details)
$ in Millions
12 Months Ended
Dec. 31, 2022
USD ($)
Dec. 31, 2021
USD ($)
Dec. 31, 2020
USD ($)
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Gross written premiums $ 4,338.7 $ 3,938.4 $ 3,698.5
Held for trading financial assets, at fair value | Recurring      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value 533.0 307.1  
Held for trading financial assets, at fair value | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value $ 533.0 $ 307.1  
Discounted cash flow | Commercial mortgage loans | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.039    
Discounted cash flow | Commercial mortgage loans | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.094    
Discounted cash flow | Commercial mortgage loans | Weighted Average | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.053    
Discounted cash flow | Commercial mortgage loans | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value $ 200.7    
Discounted cash flow | Middle market loans | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.074    
Discounted cash flow | Middle market loans | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.185    
Discounted cash flow | Middle market loans | Weighted Average | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.099    
Discounted cash flow | Middle market loans | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value $ 106.9    
Discounted cash flow | Asset-backed | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.058    
Discounted cash flow | Asset-backed | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.093    
Discounted cash flow | Asset-backed | Weighted Average | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.067    
Discounted cash flow | Global corporate securities | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.064    
Discounted cash flow | Global corporate securities | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.064    
Discounted cash flow | Global corporate securities | Weighted Average | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.064    
Discounted cash flow | Global corporate securities | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value $ 15.0    
Discounted cash flow | Equity securities — Trading | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.090    
Discounted cash flow | Equity securities — Trading | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.125    
Discounted cash flow | Equity securities — Trading | Weighted Average | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.091    
Discounted cash flow | Equity securities — Trading | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value $ 5.3    
Discounted cash flow | Short-term investments | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.064    
Discounted cash flow | Short-term investments | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.064    
Discounted cash flow | Short-term investments | Weighted Average | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.064    
Discounted cash flow | Short-term investments | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value $ 25.6    
Transaction value | Commercial mortgage loans | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value 85.8    
Transaction value | Equity securities — Trading | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value 1.3    
Liquidation method | Commercial mortgage loans | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value 25.6    
Recovery approach | Asset-backed | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value $ 66.8