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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, 2018
Dec. 31, 2017
Schedule of Trading Securities and Other Trading Items [Line Items]    
Fair Market Value $ 1,187.8 $ 1,649.3
Debt Securities, Trading, Amortized Cost 1,205.0 1,634.9
Fixed income securities - trading    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 6.3 21.5
Gross Unrealized Losses (23.5) (7.1)
Fair Market Value 1,187.8 1,649.3
Debt Securities, Trading, Amortized Cost 1,205.0 1,634.9
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 9.5 73.0
Debt Securities, Trading, Amortized Cost 9.5 73.0
Equity securities    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains   83.5
Gross Unrealized Losses   (7.3)
Fair Market Value   491.0
Debt Securities, Trading, Amortized Cost   414.8
Catastrophe Bonds    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.1 0.0
Gross Unrealized Losses (1.8) (1.1)
Fair Market Value 36.2 32.4
Debt Securities, Trading, Amortized Cost 37.9 33.5
Total - Trading    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 6.4 105.0
Gross Unrealized Losses (25.3) (15.5)
Fair Market Value 1,233.5 2,245.7
Debt Securities, Trading, Amortized Cost 1,252.4 2,156.2
U.S. government    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 1.6 0.4
Gross Unrealized Losses (0.5) (0.8)
Fair Market Value 147.7 161.9
Debt Securities, Trading, Amortized Cost 146.6 162.3
Municipal    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.0 0.0
Gross Unrealized Losses (0.1) (0.2)
Fair Market Value 2.7 32.2
Debt Securities, Trading, Amortized Cost 2.8 32.4
Corporate    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 2.6 14.0
Gross Unrealized Losses (16.6) (4.2)
Fair Market Value 720.2 1,046.3
Debt Securities, Trading, Amortized Cost 734.2 1,036.5
Non-U.S. government-backed corporate    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains   6.9
Gross Unrealized Losses   (0.5)
Fair Market Value   202.5
Debt Securities, Trading, Amortized Cost   196.1
Non-U.S government    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 1.9  
Gross Unrealized Losses (5.2)  
Fair Market Value 265.4  
Debt Securities, Trading, Amortized Cost 268.7  
Asset-backed    
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 2.4 9.9
Debt Securities, Trading, Amortized Cost 2.4 9.9
Agency mortgage-backed    
Schedule of Trading Securities and Other Trading Items [Line Items]    
Gross Unrealized Gains 0.2 0.2
Gross Unrealized Losses (1.1) (1.4)
Fair Market Value 49.4 195.5
Debt Securities, Trading, Amortized Cost $ 50.3 $ 196.7