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Investment Securities (Other long-term investments) (Details) - USD ($)
$ in Millions
Jun. 30, 2019
Dec. 31, 2018
Kudu Investment Management, LLC    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments $ 142.2 $ 0.0
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
Elementum Holdings, L.P.    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 55.1 0.0
Other unconsolidated entities    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 39.1 60.0
Kudu    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 0.0 30.7
Total unconsolidated entities    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 426.1 165.7
Hedge and private equity funds included in other long-term investments    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 166.1 146.1
Insurance-linked securities    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 40.3 0.0
Other long-term investments    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments 31.9 13.8
White Mountains    
Debt and Equity Securities, FV-NI [Line Items]    
Other Investments $ 664.4 $ 325.6