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Transactions with Related Persons (Details) (USD $)
12 Months Ended 0 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Jul. 16, 2012
Mar. 15, 2013
Related Party Transaction [Line Items]            
Purchases $ 5,602,100,000us-gaap_PaymentsToAcquireInvestments $ 4,635,500,000us-gaap_PaymentsToAcquireInvestments        
Sales of common equity securities 660,900,000wtm_ProceedsFromSaleOfTradingCommonEquitySecurities 521,100,000wtm_ProceedsFromSaleOfTradingCommonEquitySecurities 192,400,000wtm_ProceedsFromSaleOfTradingCommonEquitySecurities      
Beneficial Owner            
Related Party Transaction [Line Items]            
Per share price, class of warrant (in dollars per share)           $ 563.57us-gaap_SharePrice
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= us-gaap_BeneficialOwnerMember
Shares purchased   140,000us-gaap_TreasuryStockSharesAcquired
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= us-gaap_BeneficialOwnerMember
       
Prospector            
Related Party Transaction [Line Items]            
Asset Management Fees 6,500,000us-gaap_AssetManagementFees1
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
6,500,000us-gaap_AssetManagementFees1
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
6,400,000us-gaap_AssetManagementFees1
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
     
Performance shares granted at the beginning of each performance cycle   4,500,000wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantedAtBeginningOfPerformanceCycleToRelatedParty
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
       
Percentage of fees in excess of $500,000 revenue chargeable 6.00%wtm_PercentageOfFeesInExcessOfSpecifiedAmountOfRevenueChargeablePursuantToRevenueSharingAgreementWithRelatedParty
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
         
Amount of revenue over which 6% of fees chargeable   500,000wtm_AmountOfRevenueOverWhichSpecifiedPercentageOfFeesChargeablePursuantToRevenueSharingAgreementWithRelatedParty
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
       
Invested in limited partnership investment interests 82,400,000wtm_LimitedPartnershipInvestmentsUnderManagementCarryingAmount
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
         
Management Fees, Base Revenue 1,100,000us-gaap_ManagementFeeExpense
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
1,300,000us-gaap_ManagementFeeExpense
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
  1,100,000us-gaap_ManagementFeeExpense
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
   
Incentive fees incurred 700,000wtm_RelatedPartyTransactionIncentiveFeesFromTransactionsWithRelatedParty
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
3,200,000wtm_RelatedPartyTransactionIncentiveFeesFromTransactionsWithRelatedParty
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
  1,300,000wtm_RelatedPartyTransactionIncentiveFeesFromTransactionsWithRelatedParty
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
   
OneBeacon | Prospector            
Related Party Transaction [Line Items]            
Assets under management 431,200,000us-gaap_AssetsUnderManagementCarryingAmount
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
         
ERISA Assets 202,900,000wtm_AssetsunderManagementRelatedtoDefinedBenefitandDefinedContributionPlans
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
         
Invested in limited partnership investment interests 15,800,000wtm_LimitedPartnershipInvestmentsUnderManagementCarryingAmount
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
         
White Mountains Advisors LLC | Symetra            
Related Party Transaction [Line Items]            
Assets under management 30,900,000,000us-gaap_AssetsUnderManagementCarryingAmount
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_SymetraMember
27,800,000,000us-gaap_AssetsUnderManagementCarryingAmount
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_SymetraMember
       
Asset Management Fees 18,400,000us-gaap_AssetManagementFees1
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_SymetraMember
16,500,000us-gaap_AssetManagementFees1
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_SymetraMember
15,900,000us-gaap_AssetManagementFees1
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_SymetraMember
     
White Mountains Advisors LLC | Prospector            
Related Party Transaction [Line Items]            
Assets under management 195,700,000us-gaap_AssetsUnderManagementCarryingAmount
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
         
Oakum Bay Capital            
Related Party Transaction [Line Items]            
Ownerhsip percentage         7.50%wtm_OwnerhsipPercentageOfCommonEquity
/ dei_LegalEntityAxis
= wtm_OakumBayCapitalMember
 
Sales of common equity securities   500,000wtm_ProceedsFromSaleOfTradingCommonEquitySecurities
/ dei_LegalEntityAxis
= wtm_OakumBayCapitalMember
       
Number of years to receive portion of revenue   10 years        
Oakum Bay Capital | Director            
Related Party Transaction [Line Items]            
Related party ownerhship percentage   67.50%wtm_RelatedPartyOwnerhshipPercentage
/ dei_LegalEntityAxis
= wtm_OakumBayCapitalMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= us-gaap_DirectorMember
       
Maximum | Prospector            
Related Party Transaction [Line Items]            
Target number of performance shares granted (as a percent) 200.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardTargetedPerformanceGoalPercentageofPayoutforGrowthTargetPercentage
/ us-gaap_RangeAxis
= us-gaap_MaximumMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
         
Minimum | Prospector            
Related Party Transaction [Line Items]            
Target number of performance shares granted (as a percent) 0.00%wtm_SharebasedCompensationArrangementbySharebasedPaymentAwardTargetedPerformanceGoalPercentageofPayoutforGrowthTargetPercentage
/ us-gaap_RangeAxis
= us-gaap_MinimumMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
         
Preferred Equity Securities | Oakum Bay Capital            
Related Party Transaction [Line Items]            
Purchases         2,000,000us-gaap_PaymentsToAcquireInvestments
/ us-gaap_InvestmentTypeAxis
= wtm_PreferredEquitySecuritiesMember
/ dei_LegalEntityAxis
= wtm_OakumBayCapitalMember
 
revenue sharing agreement | Prospector            
Related Party Transaction [Line Items]            
Fees from Revenue Sharing Agreement with Related Party 400,000us-gaap_RevenueFromRelatedParties
/ us-gaap_RelatedPartyTransactionAxis
= wtm_RevenuesharingagreementMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
900,000us-gaap_RevenueFromRelatedParties
/ us-gaap_RelatedPartyTransactionAxis
= wtm_RevenuesharingagreementMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
500,000us-gaap_RevenueFromRelatedParties
/ us-gaap_RelatedPartyTransactionAxis
= wtm_RevenuesharingagreementMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
     
Trimarc Capital Fund | Oakum Bay Capital            
Related Party Transaction [Line Items]            
Management fees   100,000us-gaap_PaymentForManagementFee
/ invest_InvestmentAxis
= wtm_TrimarcCapitalFundMember
/ dei_LegalEntityAxis
= wtm_OakumBayCapitalMember
       
Trimarc Capital Fund | Hedge funds | Oakum Bay Capital            
Related Party Transaction [Line Items]            
Trading Securities, Other 7,800,000us-gaap_TradingSecuritiesOther
/ invest_InvestmentAxis
= wtm_TrimarcCapitalFundMember
/ us-gaap_InvestmentTypeAxis
= us-gaap_HedgeFundsMember
/ dei_LegalEntityAxis
= wtm_OakumBayCapitalMember
         
First Threshold Limit | White Mountains Advisors LLC | Prospector            
Related Party Transaction [Line Items]            
Assets under management 200,000,000us-gaap_AssetsUnderManagementCarryingAmount
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_FirstThresholdLimitMember
         
basis points 100.00%wtm_WTM_InvestmentAdvisoryFees
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_FirstThresholdLimitMember
         
Second Threshold Limit | White Mountains Advisors LLC | Prospector            
Related Party Transaction [Line Items]            
Assets under management 200,000,000us-gaap_AssetsUnderManagementCarryingAmount
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_SecondThresholdLimitMember
         
basis points 50.00%wtm_WTM_InvestmentAdvisoryFees
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_SecondThresholdLimitMember
         
Third Threshold Limit | White Mountains Advisors LLC | Prospector            
Related Party Transaction [Line Items]            
Assets under management 400,000,000us-gaap_AssetsUnderManagementCarryingAmount
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_ThirdThresholdLimitMember
         
basis points 25.00%wtm_WTM_InvestmentAdvisoryFees
/ dei_LegalEntityAxis
= wtm_WhiteMountainsAdvisorsLLCMember
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_ThirdThresholdLimitMember
         
Range Of Performance Cycle From 2015 to 2017 [Member] | Prospector            
Related Party Transaction [Line Items]            
Number of performance shares granted 6,250us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2015to2017Member
         
Range Of Performance Cycle From 2014-2016 [Member] | Prospector            
Related Party Transaction [Line Items]            
Number of performance shares granted 6,250us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom20142016Member
         
Performance Cycle From 2013 to 2015 | Prospector            
Related Party Transaction [Line Items]            
Number of performance shares granted 7,000us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2013To2015Member
         
Performance Cycle From 2011 to 2013 | Prospector            
Related Party Transaction [Line Items]            
Number of performance shares granted 7,750us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2011To2013Member
         
Percentage of target number granted actually received by prospector 145.50%wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesActuallyAwardedAsPercentageOfTargetAwardsGranted
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2011To2013Member
         
Payment made with respect to the performance shares granted to the related party $ 7,500,000wtm_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodPaymentMade
/ us-gaap_RelatedPartyTransactionsByRelatedPartyAxis
= wtm_ProspectorFundsMember
/ wtm_ShareBasedCompensationArrangementByPerformanceSharesAwardPerformanceCycleAxis
= wtm_RangeOfPerformanceCycleFrom2011To2013Member