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Reserves for Unpaid Losses and Loss Adjustment Expenses (Narrative) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended 9 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Sep. 30, 2014
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year $ (6.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears $ (48.4)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears $ (41.9)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears    
Increase (decrease) in reserves 1,169.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease 1,040.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease 1,193.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease    
Current Accident Year 1,175.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear 1,088.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear 1,235.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear    
Accretion of fair value adjustment to net loss and LAE reserves 0.7wtm_AccretedFairValueAdjustmentToLossAndLossAdjustmentExpenseReserves 1.7wtm_AccretedFairValueAdjustmentToLossAndLossAdjustmentExpenseReserves 10.6wtm_AccretedFairValueAdjustmentToLossAndLossAdjustmentExpenseReserves    
Un-accreted fair value, adjustment to loss and loss adjustment expense reserves, before tax 4.0wtm_UnaccretedFairValueAdjustmentToLossAndLossAdjustmentExpenseReservesBeforeTax        
Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year (98.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
(23.9)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
(34.5)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Liability for asbestos and environmental claims, gross 238.5us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
227.8us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
228.6us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
207.2us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
 
Liability for asbestos claims, net, period increase (decrease) 8.0wtm_LiabilityforAsbestosClaimsNetPeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
11.8wtm_LiabilityforAsbestosClaimsNetPeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
33.0wtm_LiabilityforAsbestosClaimsNetPeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
46.4wtm_LiabilityforAsbestosClaimsNetPeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
 
Liability for asbestos and environmental claims 210.2us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
193.9us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
189.4us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
162.7us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
 
Liability for Asbestos Claims, Net, Period Increase (Decrease) Based on Quarterly Reporting     14.0wtm_LiabilityforAsbestosClaimsNetPeriodIncreaseDecreaseBasedonQuarterlyReporting
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Liabilty for environmental claims, net, period increase (decrease) 1.6wtm_LiabiltyForEnvironmentalClaimsNetPeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
0.8wtm_LiabiltyForEnvironmentalClaimsNetPeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
0.5wtm_LiabiltyForEnvironmentalClaimsNetPeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Asbestos and Environmental Loss Three Year Survival Ratio Period 9 years 8 years      
OneBeacon          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year 75.5us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
  (7.4)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
  14.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Increase (decrease) in reserves 109.2us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
89.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
     
Current Accident Year 33.7us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
      33.7us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Liability for asbestos and environmental claims, gross 1.0us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
       
Star & Shield Insurance Exchange [Member]          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year 2.2us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_StarShieldInsuranceExchangeMember
       
Asbestos | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Liability for asbestos and environmental claims, gross 215.8us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_AsbestosIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
207.4us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_AsbestosIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
208.2us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_AsbestosIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
185.1us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_AsbestosIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
 
Liability for asbestos and environmental claims 192.8us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_AsbestosIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
178.7us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_AsbestosIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
174.2us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_AsbestosIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
146.2us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_AsbestosIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
 
Environmental | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Liability for asbestos and environmental claims, gross 22.7us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_EnvironmentalIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
20.4us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_EnvironmentalIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
20.4us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_EnvironmentalIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
22.1us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsGross
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_EnvironmentalIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
 
Liability for asbestos and environmental claims 17.4us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_EnvironmentalIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
15.2us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_EnvironmentalIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
15.2us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_EnvironmentalIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
16.5us-gaap_LiabilityForAsbestosAndEnvironmentalClaimsNet
/ us-gaap_CausesOfIncreaseDecreaseInLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAxis
= us-gaap_EnvironmentalIssueMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
 
WM Solutions | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Liability for asbestos claims, net, period increase (decrease) 22.9wtm_LiabilityforAsbestosClaimsNetPeriodIncreaseDecrease
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
13.0wtm_LiabilityforAsbestosClaimsNetPeriodIncreaseDecrease
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
11.0wtm_LiabilityforAsbestosClaimsNetPeriodIncreaseDecrease
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Liabilty for environmental claims, net, period increase (decrease) 2.1wtm_LiabiltyForEnvironmentalClaimsNetPeriodIncreaseDecrease
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
1.0wtm_LiabiltyForEnvironmentalClaimsNetPeriodIncreaseDecrease
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
0.7wtm_LiabiltyForEnvironmentalClaimsNetPeriodIncreaseDecrease
/ dei_LegalEntityAxis
= wtm_WmSolutionsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Property [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year (54.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_PropertyMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
(16.6)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_PropertyMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
(28.4)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_PropertyMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Professional Insurance | OneBeacon          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year 46.4us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_ProfessionalInsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
       
Increase (decrease) in reserves 69.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_ProfessionalInsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
59.1us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_ProfessionalInsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
     
Current Accident Year 22.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_ProfessionalInsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
       
Property, Liability and Casualty Insurance Product Line | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year (13.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
       
asbestos and environmental [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year 10.0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AsbestosandenvironmentalMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
       
Property Loss Held Above Actuarial Central Estimate [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year (24.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_PropertyLossHeldAboveActuarialCentralEstimateMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
       
Aviation Space [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year 13.0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AviationSpaceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
(10.1)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AviationSpaceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
(5.3)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AviationSpaceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Accident and Health Insurance Product Line [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year (13.0)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= us-gaap_AccidentAndHealthInsuranceSegmentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
(9.2)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= us-gaap_AccidentAndHealthInsuranceSegmentMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
     
Crop | OneBeacon          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year 0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CropinsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
       
Increase (decrease) in reserves 3.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CropinsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
0us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CropinsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
     
Current Accident Year 3.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CropinsuranceMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
       
Specialty Products | OneBeacon          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year 51.7us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
       
Increase (decrease) in reserves 80.1us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
61.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
     
Current Accident Year 28.4us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
       
Asbestos [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year   11.8us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AsbestosMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
46.4us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AsbestosMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Casualty Runoff [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year     (31.5)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_CasualtyRunoffMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Marine Energy [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year     (11.6)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_MarineEnergyMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Trade Credit [Member] | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year     (6.8)us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_TradeCreditMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Accident and Health | Sirius Group          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Prior Accident Year     4.3us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsPriorYears
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_AccidentAndHealthMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupMember
   
Management's estimate [Member] | Specialty Products | OneBeacon          
Asbestos and Environmental Loss and Loss Adjustment Expense Reserve Activity          
Current Accident Year $ 29.9us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsCurrentYear
/ us-gaap_ChangeInAccountingEstimateByTypeAxis
= wtm_ManagementsestimateMember
/ us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentAxis
= wtm_SpecialtyProductsMember
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember