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Investments in Unconsolidated Affiliates (Carrying Values of Investments) (Details) - White Mountains - USD ($)
$ in Millions
Dec. 31, 2018
Dec. 31, 2017
Schedule of Equity Method Investments [Line Items]    
Other Investments $ 325.6 $ 208.8
Limited liability companies and private equity securities    
Schedule of Equity Method Investments [Line Items]    
Other Investments 138.1 58.0
Investments accounted for under the equity method    
Schedule of Equity Method Investments [Line Items]    
Other Investments 1.3 4.6
Investments In Unconsolidated Entities    
Schedule of Equity Method Investments [Line Items]    
Other Investments 139.4 62.6
Other unconsolidated investments    
Schedule of Equity Method Investments [Line Items]    
Other Investments $ 186.2 $ 146.2