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Investment Securities (Other long-term investments) (Details) - USD ($)
$ in Millions
Mar. 31, 2018
Dec. 31, 2017
Hedge and private equity funds included in other long-term investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other Investments $ 130.6 $ 125.3
Equity method eligible private equity securities, at fair value    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other Investments 108.4 83.2
Forward Contracts    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other Investments 0.0 (3.7)
Other long-term investments    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other Investments 14.1 4.0
White Mountains    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other Investments 253.1 208.8
White Mountains | Equity method eligible private equity securities, at fair value    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Other Investments $ 84.7 $ 58.0
OneTitle    
Schedule of Trading Securities and Other Trading Assets [Line Items]    
Ownership interest (as a percent) 20.00%  
Surplus notes $ 10.0