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Significant Transactions (Details)
In Millions, unless otherwise specified
3 Months Ended 3 Months Ended 2 Months Ended 1 Months Ended 3 Months Ended 2 Months Ended
Mar. 31, 2015
USD ($)
Mar. 31, 2014
USD ($)
Dec. 31, 2014
USD ($)
Dec. 31, 2013
USD ($)
Mar. 31, 2015
Star & Shield Insurance Exchange
USD ($)
Mar. 31, 2014
QuoteLab
USD ($)
Mar. 31, 2015
QuoteLab
USD ($)
Dec. 31, 2014
QuoteLab
USD ($)
Mar. 14, 2014
QuoteLab
USD ($)
Feb. 19, 2014
WOBI
USD ($)
business
Mar. 31, 2015
WOBI
Jan. 31, 2014
Star & Shield LLC [Member]
USD ($)
Mar. 14, 2014
Common Class A
QuoteLab
Feb. 23, 2015
Common Stock
Cashboard [Member]
Feb. 19, 2014
Common Stock
WOBI
Mar. 31, 2015
Non-controlling interest
Star & Shield Insurance Exchange
USD ($)
Mar. 31, 2014
Non-controlling interest
Star & Shield Insurance Exchange
USD ($)
Feb. 19, 2014
Israel, New Shekels
Preferred Stock
WOBI
ILS
Feb. 23, 2015
Israel, New Shekels
Common Stock
Cashboard [Member]
ILS
Feb. 19, 2014
Israel, New Shekels
Common Stock
WOBI
ILS
Feb. 19, 2014
United States of America, Dollars
Preferred Stock
WOBI
USD ($)
Feb. 23, 2015
United States of America, Dollars
Common Stock
Cashboard [Member]
USD ($)
Feb. 19, 2014
United States of America, Dollars
Common Stock
WOBI
USD ($)
Feb. 23, 2015
Cashboard [Member]
USD ($)
Feb. 19, 2014
WOBI
USD ($)
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                                                  
Business Combination, Contingent Consideration, Liability             $ 7.9us-gaap_BusinessCombinationContingentConsiderationLiability
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
$ 7.9us-gaap_BusinessCombinationContingentConsiderationLiability
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
                                 
Ownership interest (as a percent)                     63.30%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_WOBIMember
  60.00%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
/ us-gaap_StatementClassOfStockAxis
= us-gaap_CommonClassAMember
56.20%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_CashboardMember
/ us-gaap_StatementClassOfStockAxis
= us-gaap_CommonStockMember
54.00%us-gaap_EquityMethodInvestmentOwnershipPercentage
/ dei_LegalEntityAxis
= wtm_WOBIMember
/ us-gaap_StatementClassOfStockAxis
= us-gaap_CommonStockMember
                   
Payments to Acquire Businesses and Interest in Affiliates 2.4us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates 32.2us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates       28.1us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
          1.8us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates
/ dei_LegalEntityAxis
= wtm_StarShieldLLCMember
          31.5us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates
/ us-gaap_CurrencyAxis
= currency_ILS
/ us-gaap_InvestmentTypeAxis
= us-gaap_PreferredStockMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
9.5us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates
/ us-gaap_CurrencyAxis
= currency_ILS
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
/ dei_LegalEntityAxis
= wtm_CashboardMember
14.4us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates
/ us-gaap_CurrencyAxis
= currency_ILS
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
9.0us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates
/ us-gaap_CurrencyAxis
= currency_USD
/ us-gaap_InvestmentTypeAxis
= us-gaap_PreferredStockMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
2.4us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates
/ us-gaap_CurrencyAxis
= currency_USD
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
/ dei_LegalEntityAxis
= wtm_CashboardMember
4.1us-gaap_PaymentsToAcquireBusinessesAndInterestInAffiliates
/ us-gaap_CurrencyAxis
= currency_USD
/ us-gaap_InvestmentTypeAxis
= us-gaap_CommonStockMember
/ dei_LegalEntityAxis
= wtm_WOBIMember
   
Premiums Written, Percentage of Total                   85.00%wtm_PremiumsWrittenPercentageOfTotal
/ dei_LegalEntityAxis
= wtm_WOBIMember
                             
Number of lines of business                   4wtm_Numberoflinesofbusiness
/ dei_LegalEntityAxis
= wtm_WOBIMember
                             
Purchase of Surplus Notes         19.0wtm_PurchaseofSurplusNotes
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
                                       
Percentage of gross profit                 62.50%wtm_Percentageofgrossprofit
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
                               
Assets 10,507.8us-gaap_Assets   10,455.7us-gaap_Assets   16.0us-gaap_Assets
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
      70.1us-gaap_Assets
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
                            5.5us-gaap_Assets
/ us-gaap_BusinessAcquisitionAxis
= wtm_CashboardMember
13.4us-gaap_Assets
/ us-gaap_BusinessAcquisitionAxis
= wtm_WOBIMember
Goodwill 169.2us-gaap_Goodwill 23.8us-gaap_Goodwill 168.9us-gaap_Goodwill 0us-gaap_Goodwill         18.3us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
5.5us-gaap_Goodwill
/ dei_LegalEntityAxis
= wtm_WOBIMember
                          0.3us-gaap_Goodwill
/ us-gaap_BusinessAcquisitionAxis
= wtm_CashboardMember
 
Intangible Assets, Net (Excluding Goodwill) 193.4us-gaap_IntangibleAssetsNetExcludingGoodwill 62.4us-gaap_IntangibleAssetsNetExcludingGoodwill 197.5us-gaap_IntangibleAssetsNetExcludingGoodwill 20.7us-gaap_IntangibleAssetsNetExcludingGoodwill                                       2.8us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_BusinessAcquisitionAxis
= wtm_CashboardMember
2.9us-gaap_IntangibleAssetsNetExcludingGoodwill
/ us-gaap_BusinessAcquisitionAxis
= wtm_WOBIMember
Goodwill and intangible assets 362.6us-gaap_IntangibleAssetsNetIncludingGoodwill   366.4us-gaap_IntangibleAssetsNetIncludingGoodwill           38.5us-gaap_IntangibleAssetsNetIncludingGoodwill
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
                               
Liabilities 5,968.0us-gaap_Liabilities   5,917.3us-gaap_Liabilities   29.5us-gaap_Liabilities
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
      10.0us-gaap_Liabilities
/ dei_LegalEntityAxis
= wtm_QuoteLabMember
0.7us-gaap_Liabilities
/ dei_LegalEntityAxis
= wtm_WOBIMember
                          1.2us-gaap_Liabilities
/ us-gaap_BusinessAcquisitionAxis
= wtm_CashboardMember
 
Net Income (Loss) Attributable to Noncontrolling Interest $ 7.3us-gaap_NetIncomeLossAttributableToNoncontrollingInterest $ 0.6us-gaap_NetIncomeLossAttributableToNoncontrollingInterest                           $ 1.1us-gaap_NetIncomeLossAttributableToNoncontrollingInterest
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
/ us-gaap_StatementEquityComponentsAxis
= us-gaap_NoncontrollingInterestMember
$ 4.6us-gaap_NetIncomeLossAttributableToNoncontrollingInterest
/ dei_LegalEntityAxis
= wtm_StarShieldInsuranceExchangeMember
/ us-gaap_StatementEquityComponentsAxis
= us-gaap_NoncontrollingInterestMember