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Investment Securities (Net 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 Gain (Loss) and Foreign Currency Gain (Loss) on Trading Securities Net of Tax $ (131,200,000) $ 193,400,000  
Fixed maturity investments      
Debt and Equity Securities, FV-NI [Line Items]      
Net Realized and Unrealized Gain (Loss) on Trading Securities 2,200,000 21,100,000  
Short-term investments      
Debt and Equity Securities, FV-NI [Line Items]      
Net Realized and Unrealized Gain (Loss) on Trading Securities 400,000 0  
Common equity securities      
Debt and Equity Securities, FV-NI [Line Items]      
Net Realized and Unrealized Gain (Loss) on Trading Securities (140,800,000) 111,300,000  
Other long-term investments      
Debt and Equity Securities, FV-NI [Line Items]      
Net Realized and Unrealized Gain (Loss) on Trading Securities (18,500,000) 113,200,000  
MediaAlpha      
Debt and Equity Securities, FV-NI [Line Items]      
Unrealized investment gain $ 30,000,000.0 $ 114,700,000 $ 180,000,000.0