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Investments in Unconsolidated Entities (Details) - White Mountains - USD ($)
$ in Millions
Sep. 30, 2019
Dec. 31, 2018
Investments in unconsolidated affiliates    
Other Investments $ 773.7 $ 325.6
Equity method eligible private equity securities, at fair value    
Investments in unconsolidated affiliates    
Other Investments 673.2 269.7
Other unconsolidated investments    
Investments in unconsolidated affiliates    
Other Investments $ 100.5 $ 55.9