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Investment Securities (Non-agency Mortgage-backed Securities) (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Investment securities      
Fair value investments $ 5,991.4us-gaap_InvestmentsFairValueDisclosure $ 6,766.5us-gaap_InvestmentsFairValueDisclosure $ 6,950.7us-gaap_InvestmentsFairValueDisclosure
Residential      
Investment securities      
Fair value investments 131.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
125.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
 
Commercial      
Investment securities      
Fair value investments 236.9us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
282.3us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
 
Total Non-agency      
Investment securities      
Fair value investments 368.1us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
408.0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
 
Securities Issued in 2004 [Member] | Residential      
Investment securities      
Fair value investments 14.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2004Member
   
Securities Issued in 2004 [Member] | Commercial      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2004Member
   
Securities Issued in 2004 [Member] | Total Non-agency      
Investment securities      
Fair value investments 14.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2004Member
   
2005 | Residential      
Investment securities      
Fair value investments 14.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2005Member
   
2005 | Commercial      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2005Member
   
2005 | Total Non-agency      
Investment securities      
Fair value investments 14.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2005Member
   
2006 | Residential      
Investment securities      
Fair value investments 9.9us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2006Member
   
2006 | Commercial      
Investment securities      
Fair value investments 8.5us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2006Member
   
2006 | Total Non-agency      
Investment securities      
Fair value investments 18.4us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2006Member
   
2007 | Residential      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2007Member
   
2007 | Commercial      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2007Member
   
2007 | Total Non-agency      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2007Member
   
2008 | Residential      
Investment securities      
Fair value investments 16.5us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2008Member
   
2008 | Commercial      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2008Member
   
2008 | Total Non-agency      
Investment securities      
Fair value investments 16.5us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2008Member
   
2009 | Residential      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2009Member
   
2009 | Commercial      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2009Member
   
2009 | Total Non-agency      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2009Member
   
2010 | Residential      
Investment securities      
Fair value investments 14.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2010Member
   
2010 | Commercial      
Investment securities      
Fair value investments 11.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2010Member
   
2010 | Total Non-agency      
Investment securities      
Fair value investments 26.4us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2010Member
   
2011 | Residential      
Investment securities      
Fair value investments 21.4us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2011Member
   
2011 | Commercial      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2011Member
   
2011 | Total Non-agency      
Investment securities      
Fair value investments 21.4us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2011Member
   
2012 | Residential      
Investment securities      
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2012Member
   
2012 | Commercial      
Investment securities      
Fair value investments 20.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2012Member
   
2012 | Total Non-agency      
Investment securities      
Fair value investments 20.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2012Member
   
2013 | Residential      
Investment securities      
Fair value investments 29.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2013Member
   
2013 | Commercial      
Investment securities      
Fair value investments 79.9us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2013Member
   
2013 | Total Non-agency      
Investment securities      
Fair value investments 109.6us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2013Member
   
2014 | Residential      
Investment securities      
Fair value investments 10.1us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2014Member
   
2014 | Commercial      
Investment securities      
Fair value investments 116.1us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2014Member
   
2014 | Total Non-agency      
Investment securities      
Fair value investments $ 126.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2014Member