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Investments in Unconsolidated Entities (Details) - White Mountains - USD ($)
$ in Millions
Jun. 30, 2020
Dec. 31, 2019
Investments in unconsolidated affiliates    
Other Investments $ 898.1 $ 856.3
Equity method eligible private equity securities, at fair value    
Investments in unconsolidated affiliates    
Other Investments 815.3 761.7
Other unconsolidated investments    
Investments in unconsolidated affiliates    
Other Investments $ 82.8 $ 94.6