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Investment Securities (Net Realized and Unrealized Investment Gains (Losses)) (Details) - USD ($)
3 Months Ended 12 Months Ended
Mar. 31, 2020
Mar. 31, 2019
Dec. 31, 2019
Debt and Equity Securities, FV-NI [Line Items]      
Net Realized and Unrealized investment (losses) gains, pre-tax $ (156,700,000) $ 245,600,000  
Tax on Net Realized and Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities (25,500,000) 52,200,000  
Net Realized and Unrealized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Net of Tax (131,200,000) 193,400,000  
MediaAlpha      
Debt and Equity Securities, FV-NI [Line Items]      
Trading securities, net realized gains   67,500,000  
Unrealized investment gain 30,000,000.0 114,700,000 $ 180,000,000.0
Foreign Currency Gain (Loss)      
Debt and Equity Securities, FV-NI [Line Items]      
Net Realized Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Net of Tax $ 400,000 $ 300,000