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Debt and Standby Letter of Credit Facilities (Debt Outstanding) (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2014
Dec. 31, 2013
Mar. 31, 2007
Oct. 10, 2014
Debt Instrument        
Debt $ 746.6us-gaap_LongTermDebt $ 676.4us-gaap_LongTermDebt    
SIG Senior Notes        
Debt Instrument        
Debt instrument at face value     400.0us-gaap_DebtInstrumentFaceAmount
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
 
Other Debt [Member]        
Debt Instrument        
Debt 4.8us-gaap_LongTermDebt
/ us-gaap_DebtInstrumentAxis
= wtm_OtherDebtMember
2.1us-gaap_LongTermDebt
/ us-gaap_DebtInstrumentAxis
= wtm_OtherDebtMember
   
OneBeacon | 2012 OBH Senior Notes        
Debt Instrument        
Debt instrument at face value 275.0us-gaap_DebtInstrumentFaceAmount
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
275.0us-gaap_DebtInstrumentFaceAmount
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
   
Unamortized original issue discount (0.3)us-gaap_DebtInstrumentUnamortizedDiscount
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
(0.3)us-gaap_DebtInstrumentUnamortizedDiscount
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
   
Debt 274.7us-gaap_LongTermDebt
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
274.7us-gaap_LongTermDebt
/ us-gaap_DebtInstrumentAxis
= wtm_A2012ObhSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_OnebeaconMember
   
Sirius Group | SIG Senior Notes        
Debt Instrument        
Debt instrument at face value 400.0us-gaap_DebtInstrumentFaceAmount
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
400.0us-gaap_DebtInstrumentFaceAmount
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
   
Unamortized original issue discount (0.3)us-gaap_DebtInstrumentUnamortizedDiscount
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
(0.4)us-gaap_DebtInstrumentUnamortizedDiscount
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
   
Debt 399.7us-gaap_LongTermDebt
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
399.6us-gaap_LongTermDebt
/ us-gaap_DebtInstrumentAxis
= wtm_SiriusGroupSeniorNotesMember
/ dei_LegalEntityAxis
= wtm_SiriusGroupMember
   
White Mountains | WTM Bank Facility        
Debt Instrument        
Debt 0us-gaap_LongTermDebt
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
0us-gaap_LongTermDebt
/ us-gaap_DebtInstrumentAxis
= wtm_WtmBankFacilityMember
/ dei_LegalEntityAxis
= wtm_WhiteMountainsMember
   
Tranzact [Member] | Tranzact Bank Facility [Member]        
Debt Instrument        
Line of Credit Facility, Fair Value of Amount Outstanding 67.4us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
  70.0us-gaap_LineOfCreditFacilityFairValueOfAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
Line of Credit Facility, Amount Outstanding 68.7us-gaap_LineOfCreditFacilityAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
0us-gaap_LineOfCreditFacilityAmountOutstanding
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
   
Unamortized Debt Issuance Expense $ (1.3)us-gaap_UnamortizedDebtIssuanceExpense
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember
$ 0us-gaap_UnamortizedDebtIssuanceExpense
/ us-gaap_DebtInstrumentAxis
= wtm_TranzactBankFacilityMember
/ dei_LegalEntityAxis
= wtm_TranzactMember