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Investments in Unconsolidated Entities - White Mountain's Investments (Details)
Mar. 31, 2020
Dec. 31, 2019
May 31, 2019
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 50.00% 50.00%  
MediaAlpha      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 48.30% 48.30%  
durchblicker      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 45.00% 45.00%  
Elementum Holdings, L.P.      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 30.00% 30.00% 30.00%
Compare.com      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 18.40% 18.40%  
JAM Partners L.P.      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent)   11.10%  
Minimum | Tuckerman Capital Funds      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 16.10% 17.50%  
Minimum | Enlightenment Capital Funds      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 9.60% 10.00%  
Minimum | Kudu Investments      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 3.20% 3.20%  
Maximum | Tuckerman Capital Funds      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 61.30% 62.40%  
Maximum | Enlightenment Capital Funds      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 36.50% 38.40%  
Maximum | Kudu Investments      
Schedule of Equity Method Investments [Line Items]      
Ownership interest (as a percent) 30.00% 30.00%