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Fair Value Measurements - Inputs Used (Details)
$ in Millions
12 Months Ended
Dec. 31, 2021
USD ($)
Dec. 31, 2020
USD ($)
Dec. 31, 2019
USD ($)
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Gross written premiums $ 3,938.4 $ 3,698.5 $ 3,442.4
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 307.1 299.3  
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 $ 307.1 $ 299.3  
Discounted cash flow | Commercial mortgage loans | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.035    
Discounted cash flow | Commercial mortgage loans | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.095    
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 0.058    
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 $ 173.9    
Discounted cash flow | Middle market loans | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.062    
Discounted cash flow | Middle market loans | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.155    
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 0.091    
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 $ 65.3    
Discounted cash flow | Asset-backed | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.030    
Discounted cash flow | Asset-backed | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.073    
Discounted cash flow | Asset-backed | Weighted Average | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.054    
Discounted cash flow | Asset-backed | Recurring | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Privately-held Investments, at fair value $ 26.7    
Discounted cash flow | Equity securities — Trading | Minimum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.092    
Discounted cash flow | Equity securities — Trading | Maximum | Level 3      
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]      
Measurement inputs 0.092    
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 0.092    
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 $ 2.8    
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 37.6    
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 0.8    
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 0.0    
Recovery approach | 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 $ 0.0