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Investment Securities - Net Realized and Unrealized Investment Gains (Losses) (Details) - USD ($)
$ in Millions
3 Months Ended 6 Months Ended
Jun. 30, 2022
Jun. 30, 2021
Jun. 30, 2022
Jun. 30, 2021
Debt and Equity Securities, FV-NI [Line Items]        
Net realized investment gains (losses) $ (2.9) $ 12.4 $ 14.5 $ 155.5
Net unrealized investment gains (losses) (217.4) 163.7 (226.5) (18.7)
Net unrealized investment gains (losses) on investment securities held at the end of the period (113.5) 113.0 (94.7) 71.3
Gain (loss) on investments, exchange rate effect (24.5) (0.2) (21.8) (0.4)
Investments Held        
Debt and Equity Securities, FV-NI [Line Items]        
Net realized and unrealized investment gains (losses) (217.6) 172.6 (207.2) 132.0
Fixed maturity investments        
Debt and Equity Securities, FV-NI [Line Items]        
Net realized investment gains (losses) (4.8) 0.9 (5.9) 2.8
Net unrealized investment gains (losses) (54.6) 8.2 (134.1) (19.2)
Short-term investments        
Debt and Equity Securities, FV-NI [Line Items]        
Net realized investment gains (losses) (0.1) 0.6 (0.3) 0.3
Net unrealized investment gains (losses) (0.7) 1.0 (0.5) 0.0
Common equity securities        
Debt and Equity Securities, FV-NI [Line Items]        
Net realized investment gains (losses) 0.0 0.4 0.0 0.4
Net unrealized investment gains (losses) (11.6) 4.6 (10.6) 5.6
Net unrealized investment gains (losses) on investment securities held at the end of the period (11.6) 5.0 (10.6) 6.0
Marketing Technology (MediaAlpha)        
Debt and Equity Securities, FV-NI [Line Items]        
Net realized investment gains (losses) 0.0 0.0 0.0 160.3
Net unrealized investment gains (losses) (113.5) 113.0 (94.7) (89.0)
Net unrealized investment gains (losses) on investment securities held at the end of the period (113.5) 113.0 (94.7) 71.3
Other long-term investments        
Debt and Equity Securities, FV-NI [Line Items]        
Net realized investment gains (losses) 2.0 10.5 20.7 (8.3)
Net unrealized investment gains (losses) (37.0) 36.9 13.4 83.9
Net realized and unrealized investment (losses) gains        
Debt and Equity Securities, FV-NI [Line Items]        
Net unrealized investment gains (losses) on investment securities held at the end of the period (220.3) 176.1 (212.0) 136.8
TPC Providers        
Debt and Equity Securities, FV-NI [Line Items]        
Net unrealized investment gains (losses) on investment securities held at the end of the period 2.7 (3.5) 4.8 (4.8)
Fixed maturity and short-term investments        
Debt and Equity Securities, FV-NI [Line Items]        
Net unrealized investment gains (losses) on investment securities held at the end of the period (60.2) 10.7 (140.8) (16.1)
Net realized and unrealized investment gains (losses) (2.1) (0.3) (3.1) (1.3)
Fixed maturity and short-term investments | Investments Held        
Debt and Equity Securities, FV-NI [Line Items]        
Net unrealized investment gains (losses) on investment securities held at the end of the period (58.1) 11.0 (137.7) (14.8)
Common equity securities and investment in MediaAlpha        
Debt and Equity Securities, FV-NI [Line Items]        
Net unrealized investment gains (losses) on investment securities held at the end of the period (125.1) 118.0 (105.3) 77.3
Net realized and unrealized investment gains (losses) 0.0 0.0 0.0 (19.9)
Common equity securities and investment in MediaAlpha | Investments Held        
Debt and Equity Securities, FV-NI [Line Items]        
Net unrealized investment gains (losses) on investment securities held at the end of the period $ (125.1) $ 118.0 $ (105.3) $ 57.4