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Investments in Unconsolidated Affiliates (Investments in Symetra Table Rollforward) (Details) (USD $)
In Millions, except Per Share data, unless otherwise specified
3 Months Ended
Mar. 31, 2015
Mar. 31, 2014
Changes in carrying value of investment in Symetra    
Carrying value at the beginning of the period $ 414.4wtm_InvestmentsInUnconsolidatedAffiliates  
Equity in earnings 7.3us-gaap_IncomeLossFromEquityMethodInvestments 13.8us-gaap_IncomeLossFromEquityMethodInvestments
Carrying value at the end of the period 450.8wtm_InvestmentsInUnconsolidatedAffiliates  
Income Tax Expense (Benefit) 25.0us-gaap_IncomeTaxExpenseBenefit 30.9us-gaap_IncomeTaxExpenseBenefit
Symetra | Common Stock    
Investments in unconsolidated affiliates    
Share Price $ 23.46us-gaap_SharePrice
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
 
Changes in carrying value of investment in Symetra    
Carrying value at the beginning of the period 411.4wtm_InvestmentsInUnconsolidatedAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
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317.3wtm_InvestmentsInUnconsolidatedAffiliates
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= wtm_SymetraMember
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= us-gaap_CommonStockMember
Equity in earnings 7.2us-gaap_IncomeLossFromEquityMethodInvestments
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14.4us-gaap_IncomeLossFromEquityMethodInvestments
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Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio 30.9wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio
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39.3wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio
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Dividends received (2.2)us-gaap_EquityMethodInvestmentDividendsOrDistributions
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(2.0)us-gaap_EquityMethodInvestmentDividendsOrDistributions
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Carrying value at the end of the period 447.3wtm_InvestmentsInUnconsolidatedAffiliates
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= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
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369.0wtm_InvestmentsInUnconsolidatedAffiliates
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Aggregate value of White Mountains common shares of Symetra at quoted market price 470.3wtm_InvestmentsInUnconsolidatedAffiliatesAtQuotedMarketPrice
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White Mountains | Common Stock    
Changes in carrying value of investment in Symetra    
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio 68.4wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
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39.3wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio
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= wtm_WhiteMountainsMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
equity in earnings of unconsolidated affiliates | Symetra | Common Stock    
Changes in carrying value of investment in Symetra    
Income Tax Expense (Benefit) 0.4us-gaap_IncomeTaxExpenseBenefit
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
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1.0us-gaap_IncomeTaxExpenseBenefit
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Net unrealized gains (losses) of unconsolidated affiliates | White Mountains | Common Stock    
Changes in carrying value of investment in Symetra    
Income Tax Expense (Benefit) 4.6us-gaap_IncomeTaxExpenseBenefit
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2.8us-gaap_IncomeTaxExpenseBenefit
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Amortization of common share basis difference | Symetra | Common Stock    
Changes in carrying value of investment in Symetra    
Equity in earnings 0.7us-gaap_IncomeLossFromEquityMethodInvestments
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0.7us-gaap_IncomeLossFromEquityMethodInvestments
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impairment of net unrealized gains (losses) | Net unrealized gains (losses) of unconsolidated affiliates | Symetra | Common Stock    
Changes in carrying value of investment in Symetra    
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio $ 2.9wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio
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/ us-gaap_StatementEquityComponentsAxis
= wtm_NetunrealizedgainslossesofunconsolidatedaffiliatesMember
$ 3.1wtm_EquityMethodInvestmentInvesteeUnrealizedGainsLossesPortfolio
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