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Investment Securities (Other long-term investments) (Details) - USD ($)
$ in Millions
Mar. 31, 2019
Dec. 31, 2018
MediaAlpha    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments $ 114.7 $ 0.0
DavidShield & PassportCard    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 75.0 75.0
Kudu Investment Management, LLC    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 71.7 30.7
Other unconsolidated entities    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 54.4 60.0
Total unconsolidated entities    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 315.8 165.7
Hedge and private equity funds included in other long-term investments    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 150.7 146.1
Other long-term investments    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 31.1 13.8
White Mountains    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments $ 497.6 $ 325.6