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Investments in Unconsolidated Affiliates (Symetra Narrative) (Details) (USD $)
In Millions, except Share data, unless otherwise specified
12 Months Ended 6 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Jun. 20, 2013
Investments in unconsolidated affiliates          
Common shares repurchased and retired during the period   1,329,640us-gaap_StockRepurchasedAndRetiredDuringPeriodShares      
Treasury Stock Acquired, Average Cost Per Share $ 617.00us-gaap_TreasuryStockAcquiredAverageCostPerShare $ 564.00us-gaap_TreasuryStockAcquiredAverageCostPerShare $ 503.00us-gaap_TreasuryStockAcquiredAverageCostPerShare    
Symetra          
Investments in unconsolidated affiliates          
Shares of symetra financial corporation owned (in shares) 20,050,000us-gaap_InvestmentsInAndAdvancesToAffiliatesBalanceShares
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
       
Ownership interest (as a percent) 17.31%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
17.03%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
     
Dividends received $ (34.1)us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
$ (6.4)us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
$ (4.9)us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
   
Investments in unconsolidated affiliates on conversion of warrants     9,490,000wtm_InvestmentsInUnconsolidatedAffiliatesOnConversionOfWarrants
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
  2,650,000wtm_InvestmentsInUnconsolidatedAffiliatesOnConversionOfWarrants
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
Gain (Loss) on Warrants   10.8wtm_GainLossOnWarrants
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
17.7wtm_GainLossOnWarrants
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
   
Fair value of investment       261.0us-gaap_EquityMethodInvestmentsFairValueDisclosure
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
 
Estimated fair value of investment per share       $ 15wtm_EquityMethodInvestmentsFairValuePerShare
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
 
After-tax equity in losses of unconsolidated affiliates       45.9wtm_ImpairmentOfCommonSharesEquityInEarningsAfterTax
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
 
Equity in net unrealized losses increase relating to amortization of common share impairment       136.6wtm_Othercomprehensiveincomeincreaserelatingtoamortizartionofcommonsharebasisdifference
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
 
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity 2.4us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
      19.3us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity, Attributable to Equity Earnings in Affiliates 0.5wtm_EquityMethodInvestmentDifferenceBetweenCarryingAmountandUnderlyingEquityAttributabletoEquityEarningsinAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
       
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity, Net Unrealized Gains and Losses of Affiliate 1.9wtm_EquityMethodInvestmentDifferenceBetweenCarryingAmountandUnderlyingEquityNetUnrealizedGainsandLossesofAffiliate
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
       
Term of amortization (in years)     30 years    
Weight Average Years Remaining 28 years        
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity, Unamortized Basis Difference Attributable to Equity Earnings 36.4wtm_EquityMethodInvestmentDifferenceBetweenCarryingAmountandUnderlyingEquityUnamortizedBasisDifferenceAttributabletoEquityEarnings
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
       
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity, Unamortized Basis Difference Attributable to Unrealized Gains in Affiliates 134.0wtm_EquityMethodInvestmentDifferenceBetweenCarryingAmountandUnderlyingEquityUnamortizedBasisDifferenceAttributabletoUnrealizedGainsinAffiliates
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
       
Common Stock | Symetra          
Investments in unconsolidated affiliates          
Dividends received (34.1)us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
(6.4)us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
(4.9)us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
   
Per share price, class of warrant (in dollars per share) $ 23.05us-gaap_SharePrice
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
       
Gain (Loss) on Warrants   0wtm_GainLossOnWarrants
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
0wtm_GainLossOnWarrants
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
   
Warrants          
Investments in unconsolidated affiliates          
Gain (Loss) on Warrants         10.8wtm_GainLossOnWarrants
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
Warrants | Symetra          
Investments in unconsolidated affiliates          
Dividends received 0us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
0us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
0us-gaap_EquityMethodInvestmentDividendsOrDistributions
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
   
Per share price, class of warrant (in dollars per share)     $ 11.49us-gaap_SharePrice
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
   
Gain (Loss) on Warrants   10.8wtm_GainLossOnWarrants
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
17.7wtm_GainLossOnWarrants
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
   
Cash dividends received on warrants         1.5us-gaap_ProceedsFromDividendsReceived
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_WarrantMember
Symetra | Common Stock          
Investments in unconsolidated affiliates          
Common shares repurchased and retired during the period         6,600,000us-gaap_StockRepurchasedAndRetiredDuringPeriodShares
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
/ dei_LegalEntityAxis
= wtm_SymetraMember
Treasury Stock Acquired, Average Cost Per Share         $ 13.44us-gaap_TreasuryStockAcquiredAverageCostPerShare
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
/ dei_LegalEntityAxis
= wtm_SymetraMember
equity in earnings of unconsolidated affiliates [Member] | Symetra          
Investments in unconsolidated affiliates          
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity 170.4us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_StatementEquityComponentsAxis
= wtm_EquityinearningsofunconsolidatedaffiliatesMember
      0.4us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_StatementEquityComponentsAxis
= wtm_EquityinearningsofunconsolidatedaffiliatesMember
After tax amortization through equity in earnings 2.8wtm_InvestmentsInUnconsolidatedAffiliatesAmortizationThroughEquityInEarningsAfterTax
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_StatementEquityComponentsAxis
= wtm_EquityinearningsofunconsolidatedaffiliatesMember
       
Net unrealized gains (losses) of unconsolidated affiliates [Member] | Symetra          
Investments in unconsolidated affiliates          
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity         18.9us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_StatementEquityComponentsAxis
= wtm_NetunrealizedgainslossesofunconsolidatedaffiliatesMember
After tax amortization through equity in net unrealized losses $ 11.7wtm_InvestmentsInUnconsolidatedAffiliatesAmortizationThroughEquityInNetUnrealizedLossesAfterTax
/ us-gaap_InvestmentsInAndAdvancesToAffiliatesCategorizationAxis
= wtm_SymetraMember
/ us-gaap_StatementEquityComponentsAxis
= wtm_NetunrealizedgainslossesofunconsolidatedaffiliatesMember