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Goodwill and Other Intangible Assets (Goodwill and Intangible Assets) (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Oct. 10, 2014
Mar. 14, 2014
Feb. 19, 2014
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) $ 213.5us-gaap_IntangibleAssetsGrossExcludingGoodwill $ 25.0us-gaap_IntangibleAssetsGrossExcludingGoodwill        
Amortization of Intangible Assets 16.0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization 4.3us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization        
Intangible Assets, Net (Excluding Goodwill) 197.5us-gaap_IntangibleAssetsNetExcludingGoodwill 20.7us-gaap_IntangibleAssetsNetExcludingGoodwill 16.9us-gaap_IntangibleAssetsNetExcludingGoodwill      
Goodwill 168.9us-gaap_Goodwill 0us-gaap_Goodwill 0us-gaap_Goodwill      
Intangible Assets, Gross (Including Goodwill) 382.4wtm_IntangibleAssetsGrossIncludingGoodwill 25.0wtm_IntangibleAssetsGrossIncludingGoodwill        
Goodwill and intangible assets 366.4us-gaap_IntangibleAssetsNetIncludingGoodwill 20.7us-gaap_IntangibleAssetsNetIncludingGoodwill        
Tranzact [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 146.3us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Amortization of Intangible Assets 3.5us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Intangible Assets, Net (Excluding Goodwill) 142.8us-gaap_IntangibleAssetsNetExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_TranzactMember
  146.3us-gaap_IntangibleAssetsNetExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_TranzactMember
   
Goodwill 145.1us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_TranzactMember
  145.1us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_TranzactMember
   
QuoteLab [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 38.5us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
       
Amortization of Intangible Assets 6.0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
       
Intangible Assets, Net (Excluding Goodwill) 32.5us-gaap_IntangibleAssetsNetExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
    38.5us-gaap_IntangibleAssetsNetExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
 
Goodwill 18.3us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
    18.3us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
 
WOBI [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 2.9us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Amortization of Intangible Assets 0.4us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Intangible Assets, Net (Excluding Goodwill) 2.5us-gaap_IntangibleAssetsNetExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Goodwill 5.5us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_WOBIMember
      5.5us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_WOBIMember
Developed Technology Rights [Member] | Tranzact [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 12.7us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Amortization of Intangible Assets 0.5us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Intangible Assets, Net (Excluding Goodwill) 12.2us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 5 years          
Developed Technology Rights [Member] | QuoteLab [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 32.0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
       
Amortization of Intangible Assets 4.8us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
       
Intangible Assets, Net (Excluding Goodwill) 27.2us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 5 years          
Developed Technology Rights [Member] | WOBI [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 0.8us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Amortization of Intangible Assets 0.2us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Intangible Assets, Net (Excluding Goodwill) 0.6us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_DevelopedTechnologyRightsMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 3 years          
Customer Relationships [Member]            
Goodwill [Line Items]            
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 3 years          
Customer Relationships [Member] | Tranzact [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 107.5us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Amortization of Intangible Assets 2.1us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Intangible Assets, Net (Excluding Goodwill) 105.4us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 10 years          
Customer Relationships [Member] | QuoteLab [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 6.5us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
       
Amortization of Intangible Assets 1.2us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
       
Intangible Assets, Net (Excluding Goodwill) 5.3us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 4 years          
Customer Relationships [Member] | Star & Shield Insurance Exchange [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 1.2us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
       
Amortization of Intangible Assets 0.4us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
       
Intangible Assets, Net (Excluding Goodwill) 0.8us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_CustomerRelationshipsMember
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
       
Trademarks [Member] | WOBI [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 2.1us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TrademarksMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TrademarksMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Amortization of Intangible Assets 0.2us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TrademarksMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TrademarksMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Intangible Assets, Net (Excluding Goodwill) 1.9us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TrademarksMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TrademarksMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 8 years          
Other Intangible Assets [Member] | Tranzact [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 0.5us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Amortization of Intangible Assets 0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Intangible Assets, Net (Excluding Goodwill) 0.5us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 7 years          
Other Intangible Assets [Member] | OneBeacon            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 9.4us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
9.4us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
       
Amortization of Intangible Assets 5.7us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
4.3us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
       
Intangible Assets, Net (Excluding Goodwill) 3.7us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
5.1us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_OtherIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 10 years          
Trade Names [Member] | Tranzact [Member]            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 25.6us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TradeNamesMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TradeNamesMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Amortization of Intangible Assets 0.9us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TradeNamesMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TradeNamesMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Intangible Assets, Net (Excluding Goodwill) 24.7us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TradeNamesMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_TradeNamesMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
       
Acquired Finite-lived Intangible Assets, Weighted Average Useful Life 6 years          
Contract-Based Intangible Assets [Member] | Sirius Group            
Goodwill [Line Items]            
Intangible Assets, Gross (Excluding Goodwill) 15.2us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_ContractBasedIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
15.6us-gaap_IntangibleAssetsGrossExcludingGoodwill
/ us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_ContractBasedIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
       
Amortization of Intangible Assets 0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_ContractBasedIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
0us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization
/ us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_ContractBasedIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
       
Intangible Assets, Net (Excluding Goodwill) $ 15.2us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_ContractBasedIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
$ 15.6us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis
= us-gaap_ContractBasedIntangibleAssetsMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember