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Reserves for Unpaid Losses and Loss Adjustment Expenses (Reserve Summary) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Dec. 31, 2010
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]          
Gross beginning balance $ 3,079.3us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense $ 3,168.9us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense $ 5,702.3us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense    
Less beginning reinsurance recoverable on unpaid losses (428.1)us-gaap_ReinsuranceReceivablesIncurredButNotReportedClaims (429.1)us-gaap_ReinsuranceReceivablesIncurredButNotReportedClaims (2,507.3)us-gaap_ReinsuranceReceivablesIncurredButNotReportedClaims    
Net loss and LAE reserves 2,651.2us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet 2,739.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet 3,195.0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet    
Current Accident Year 1,175.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear 1,088.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear 1,235.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear    
Prior Accident Year (6.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears (48.4)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears (41.9)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears    
Total incurred losses and LAE 1,169.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease 1,040.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease 1,193.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease    
Accretion of fair value adjustment to net loss and LAE reserves 0.7wtm_AccretedFairValueAdjustmentToLossAndLossAdjustmentExpenseReserves 1.7wtm_AccretedFairValueAdjustmentToLossAndLossAdjustmentExpenseReserves 10.6wtm_AccretedFairValueAdjustmentToLossAndLossAdjustmentExpenseReserves    
Foreign currency translation adjustment to net loss and LAE reserves (36.0)wtm_ForeignCurrencyTranslationAdjustmentToLossAndLossAdjustmentExpenseReserves 0.3wtm_ForeignCurrencyTranslationAdjustmentToLossAndLossAdjustmentExpenseReserves 12.9wtm_ForeignCurrencyTranslationAdjustmentToLossAndLossAdjustmentExpenseReserves    
Loss and LAE paid relating to current year losses (345.3)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear (336.2)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear (404.7)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear    
Loss and LAE paid relating to prior year losses (823.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears (832.6)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears (901.6)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears    
Total loss and LAE payments (1,168.3)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaid (1,168.8)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaid (1,306.3)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaid    
Net loss and LAE reserves 2,675.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet 2,651.2us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet 2,739.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet    
Plus ending reinsurance recoverable on unpaid losses 483.9us-gaap_ReinsuranceReceivablesIncurredButNotReportedClaims 428.1us-gaap_ReinsuranceReceivablesIncurredButNotReportedClaims 429.1us-gaap_ReinsuranceReceivablesIncurredButNotReportedClaims    
Gross ending balance 3,159.8us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense 3,079.3us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense 3,168.9us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense    
AutoOne          
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]          
Net loss and LAE reserves       0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet
/ dei_LegalEntityAxis
= wtm_AutoOneMember
(383.3)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet
/ dei_LegalEntityAxis
= wtm_AutoOneMember
Net loss and LAE reserves   0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet
/ dei_LegalEntityAxis
= wtm_AutoOneMember
  0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet
/ dei_LegalEntityAxis
= wtm_AutoOneMember
(383.3)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet
/ dei_LegalEntityAxis
= wtm_AutoOneMember
Sirius Group          
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]          
Loss and LAE reserves acquired 45.4wtm_LossAndLossAdjustmentExpenseReservesAcquired
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
37.7wtm_LossAndLossAdjustmentExpenseReservesAcquired
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
17.0wtm_LossAndLossAdjustmentExpenseReservesAcquired
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
   
Star & Shield Insurance Exchange [Member]          
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]          
Loss and LAE reserves consolidated — SSIE $ 13.6wtm_LossAndLossAdjustmentExpenseReservesSold
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
$ 0wtm_LossAndLossAdjustmentExpenseReservesSold
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
$ 0wtm_LossAndLossAdjustmentExpenseReservesSold
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember