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Investments in Unconsolidated Entities (Details) - White Mountains - USD ($)
$ in Millions
Mar. 31, 2020
Dec. 31, 2019
Investments in unconsolidated affiliates    
Other Investments $ 805.6 $ 856.3
Equity method eligible private equity securities, at fair value    
Investments in unconsolidated affiliates    
Other Investments 718.0 761.7
Other unconsolidated investments    
Investments in unconsolidated affiliates    
Other Investments $ 87.6 $ 94.6