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Investments - Cost, Gross Unrealized Gains and Losses, and Estimated Fair Value of Trading Investments in Fixed Income Maturities (Details) - USD ($)
$ in Millions
Dec. 31, 2019
Dec. 31, 2018
Schedule of Trading Securities and Other Trading Items [Line Items]    
Debt Securities, Trading, Amortized Cost $ 1,106.6 $ 1,205.0
Fixed income securities - trading    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 24.2 6.3
Gross Unrealized Losses (2.0) (23.5)
Fair market value, trading 1,128.8 1,187.8
Debt Securities, Trading, Amortized Cost 1,106.6 1,205.0
Short-term investments    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.0 0.0
Gross Unrealized Losses 0.0 0.0
Fair market value, trading 79.2 9.5
Debt Securities, Trading, Amortized Cost 79.2 9.5
Equity securities — Trading    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.2  
Gross Unrealized Losses 0.0  
Fair market value, trading 2.7  
Debt Securities, Trading, Amortized Cost 2.5  
Catastrophe Bonds    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.0 0.1
Gross Unrealized Losses (0.8) (1.8)
Fair market value, trading 28.6 36.2
Debt Securities, Trading, Amortized Cost 29.4 37.9
Commercial mortgage loans    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.3  
Gross Unrealized Losses 0.0  
Fair market value, trading 156.6  
Debt Securities, Trading, Amortized Cost 156.3  
Middle market loans    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.2  
Gross Unrealized Losses (0.2)  
Fair market value, trading 111.7  
Debt Securities, Trading, Amortized Cost 111.7  
Securities, asset-backed    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.0  
Gross Unrealized Losses 0.0  
Fair market value, trading 8.7  
Debt Securities, Trading, Amortized Cost 8.7  
Privately-held investments    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.7  
Gross Unrealized Losses (0.2)  
Fair market value, trading 279.7 0.0
Debt Securities, Trading, Amortized Cost 279.2  
Total - Trading    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 24.9 6.4
Gross Unrealized Losses (3.0) (25.3)
Fair market value, trading 1,516.3 1,233.5
Debt Securities, Trading, Amortized Cost 1,494.4 1,252.4
U.S. government    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 1.8 1.6
Gross Unrealized Losses (0.1) (0.5)
Fair market value, trading 185.0 147.7
Debt Securities, Trading, Amortized Cost 183.3 146.6
Municipal    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.1 0.0
Gross Unrealized Losses 0.0 (0.1)
Fair market value, trading 3.2 2.7
Debt Securities, Trading, Amortized Cost 3.1 2.8
Corporate    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 11.6 2.6
Gross Unrealized Losses (0.1) (16.6)
Fair market value, trading 243.2 720.2
Debt Securities, Trading, Amortized Cost 231.7 734.2
Non-U.S government    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 7.4 1.9
Gross Unrealized Losses (0.1) (5.2)
Fair market value, trading 151.2 265.4
Debt Securities, Trading, Amortized Cost 143.9 268.7
Asset-backed    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 2.4 0.0
Gross Unrealized Losses (1.7) 0.0
Fair market value, trading 492.4 2.4
Debt Securities, Trading, Amortized Cost 491.7 2.4
Agency mortgage-backed    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.9 0.2
Gross Unrealized Losses 0.0 (1.1)
Fair market value, trading 53.8 49.4
Debt Securities, Trading, Amortized Cost $ 52.9 $ 50.3