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Investments - Other Investments (Details) - USD ($)
$ in Millions
1 Months Ended 12 Months Ended
Dec. 14, 2020
Jul. 26, 2016
Mar. 31, 2021
Jan. 31, 2015
Dec. 31, 2021
Dec. 31, 2020
Dec. 31, 2019
Dec. 31, 2018
Equity Method Investment, Aggregate Cost [Roll Forward]                
Opening undistributed value of investment, beginning balance         $ 0.9 $ 67.9    
Investment in the period         3.2 0.5    
Equity method investment, realized gain (loss) on disposal           10.4    
Proceeds from Sale of Equity Method Investments         3.9      
Closing value of investment, ending balance           0.9 $ 67.9  
Equity Method Investment, Nonconsolidated Investee, Other                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Unrealized Gain (Loss) on Investments         0.3 (0.7)    
Proceeds from Sale of Equity Method Investments         (0.5) (77.2)    
MVI                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Opening undistributed value of investment, beginning balance         0.0 0.4    
Investment in the period     $ 0.8 $ 0.8 0.4 0.0 0.2 $ 0.1
Equity method investment, realized gain (loss) on disposal           0.0    
Proceeds from Sale of Equity Method Investments         0.5      
Closing value of investment, ending balance           0.0 0.4  
MVI | Equity Method Investment, Nonconsolidated Investee, Other                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Unrealized Gain (Loss) on Investments         0.1 (0.4)    
Proceeds from Sale of Equity Method Investments         0.0 0.0    
Multi-Line Insurer                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Opening undistributed value of investment, beginning balance         0.5 0.0    
Investment in the period         2.5 0.5    
Equity method investment, realized gain (loss) on disposal           0.0    
Proceeds from Sale of Equity Method Investments         3.2      
Closing value of investment, ending balance           0.5 0.0  
Multi-Line Insurer | Equity Method Investment, Nonconsolidated Investee, Other                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Unrealized Gain (Loss) on Investments         0.2 0.0    
Proceeds from Sale of Equity Method Investments         0.0 0.0    
Bene                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Opening undistributed value of investment, beginning balance         0.0 4.3    
Investment in the period   $ 3.3            
Equity method investment, cash payment         0.0 0.0 1.1 $ 1.2
Equity method investment, realized gain (loss) on disposal           1.8    
Proceeds from Sale of Equity Method Investments         0.0      
Closing value of investment, ending balance           0.0 4.3  
Bene | Equity Method Investment, Nonconsolidated Investee, Other                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Unrealized Gain (Loss) on Investments         0.0 0.0    
Proceeds from Sale of Equity Method Investments         0.0 (6.1)    
Digital Re                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Opening undistributed value of investment, beginning balance         0.4 0.7    
Investment in the period         0.3 0.0    
Equity method investment, realized gain (loss) on disposal           0.0    
Proceeds from Sale of Equity Method Investments         0.2      
Closing value of investment, ending balance           0.4 0.7  
Digital Re | Equity Method Investment, Nonconsolidated Investee, Other                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Unrealized Gain (Loss) on Investments         0.0 (0.3)    
Proceeds from Sale of Equity Method Investments         (0.5) 0.0    
Crop Re                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Opening undistributed value of investment, beginning balance         0.0 62.5    
Investment in the period         0.0 0.0    
Equity method investment, realized gain (loss) on disposal $ 71.1         8.6    
Proceeds from Sale of Equity Method Investments         0.0      
Closing value of investment, ending balance           0.0 $ 62.5  
Crop Re | Equity Method Investment, Nonconsolidated Investee, Other                
Equity Method Investment, Aggregate Cost [Roll Forward]                
Unrealized Gain (Loss) on Investments         0.0 0.0    
Proceeds from Sale of Equity Method Investments         $ 0.0 $ (71.1)