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Investment Securities (Net Unrealized Investment Gains (Losses)) (Details) - USD ($)
3 Months Ended 6 Months Ended 12 Months Ended
Jun. 30, 2020
Jun. 30, 2019
Mar. 31, 2019
Jun. 30, 2020
Jun. 30, 2019
Dec. 31, 2019
Debt and Equity Securities, FV-NI [Line Items]            
Net Realized and Unrealized Gain (Loss) on Trading Securities $ 152,900,000 $ 35,200,000   $ (3,800,000) $ 280,800,000  
Trading Securities, Realized and Unrealized Gain (Loss) 2,200,000 200,000   (6,500,000) 12,400,000  
Fixed maturity investments            
Debt and Equity Securities, FV-NI [Line Items]            
Net Realized and Unrealized Gain (Loss) on Trading Securities 30,000,000.0 16,900,000   32,200,000 38,000,000.0  
Short-term investments            
Debt and Equity Securities, FV-NI [Line Items]            
Net Realized and Unrealized Gain (Loss) on Trading Securities 0 300,000   400,000 300,000  
Common equity securities            
Debt and Equity Securities, FV-NI [Line Items]            
Net Realized and Unrealized Gain (Loss) on Trading Securities 98,300,000 27,800,000   (42,500,000) 139,100,000  
Other long-term investments            
Debt and Equity Securities, FV-NI [Line Items]            
Net Realized and Unrealized Gain (Loss) on Trading Securities 24,600,000 (9,800,000)   6,100,000 103,400,000  
MediaAlpha            
Debt and Equity Securities, FV-NI [Line Items]            
Unrealized investment gain 15,000,000.0   $ 114,700,000 45,000,000.0 114,700,000 $ 180,000,000.0
Trading Securities, Realized and Unrealized Gain (Loss)         67,500,000  
Investments Held [Member]            
Debt and Equity Securities, FV-NI [Line Items]            
Net Realized and Unrealized Gain (Loss) on Trading Securities $ 150,700,000 $ 35,000,000.0   $ 2,700,000 $ 268,400,000