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Investment Securities (Non-agency Mortgage-backed Securities) (Details) (USD $)
In Millions, unless otherwise specified
Mar. 31, 2015
Dec. 31, 2014
Mar. 31, 2014
Dec. 31, 2013
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments $ 5,957.2us-gaap_InvestmentsFairValueDisclosure $ 5,991.4us-gaap_InvestmentsFairValueDisclosure $ 6,736.7us-gaap_InvestmentsFairValueDisclosure $ 6,766.5us-gaap_InvestmentsFairValueDisclosure
Commercial Mortgage Backed Securities Fixed Rate [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 165.6us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_CommercialMortgageBackedSecuritiesFixedRateMember
     
Commercial Mortgage Backed Securities Floating Rate [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 126.6us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_CommercialMortgageBackedSecuritiesFloatingRateMember
     
Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 194.3us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
131.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
   
Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 292.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
236.9us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
   
Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 486.5us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
368.1us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
   
Securities Issued in 2004 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 35.0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2004Member
     
Securities Issued in 2004 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2004Member
     
Securities Issued in 2004 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 35.0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2004Member
     
Securities Issued in 2005 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 13.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2005Member
     
Securities Issued in 2005 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2005Member
     
Securities Issued in 2005 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 13.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2005Member
     
Securities Issued In 2006 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 9.3us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2006Member
     
Securities Issued In 2006 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 8.4us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2006Member
     
Securities Issued In 2006 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 17.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2006Member
     
Securities Issued In 2007 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2007Member
     
Securities Issued In 2007 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2007Member
     
Securities Issued In 2007 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2007Member
     
Securities Issued In 2008 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 15.8us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2008Member
     
Securities Issued In 2008 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2008Member
     
Securities Issued In 2008 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 15.8us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2008Member
     
Securities Issued In 2009 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2009Member
     
Securities Issued In 2009 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2009Member
     
Securities Issued In 2009 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2009Member
     
Securities Issued In 2010 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 57.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2010Member
     
Securities Issued In 2010 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 11.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2010Member
     
Securities Issued In 2010 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 68.9us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2010Member
     
Securities Issued In 2011 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 20.1us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2011Member
     
Securities Issued In 2011 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2011Member
     
Securities Issued In 2011 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 20.1us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2011Member
     
Securities Issued in 2012 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 4.6us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2012Member
     
Securities Issued in 2012 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 26.1us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2012Member
     
Securities Issued in 2012 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 30.7us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2012Member
     
Securities Issued in 2013 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 28.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2013Member
     
Securities Issued in 2013 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 88.6us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2013Member
     
Securities Issued in 2013 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 116.8us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedIn2013Member
     
Securities Issued in 2014 | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 9.9us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2014Member
     
Securities Issued in 2014 | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 122.3us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2014Member
     
Securities Issued in 2014 | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 132.2us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2014Member
     
Securities Issued in 2015 [Member] | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2015Member
     
Securities Issued in 2015 [Member] | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 35.6us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2015Member
     
Securities Issued in 2015 [Member] | Mortgage-backed Securities, Issued by Private Enterprises        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 35.6us-gaap_InvestmentsFairValueDisclosure
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_MortgageBackedSecuritiesIssuedByPrivateEnterprisesMember
/ wtm_SecurityIssuanceYearAxis
= wtm_SecuritiesIssuedin2015Member
     
Subordinate | Commercial Mortgage Backed Securities Fixed Rate [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 70.8us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_CommercialMortgageBackedSecuritiesFixedRateMember
     
Subordinate | Commercial Mortgage Backed Securities Floating Rate [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 126.6us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_CommercialMortgageBackedSecuritiesFloatingRateMember
     
Subordinate | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
     
Subordinate | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 197.4us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SubordinateMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
     
Super Senior | Commercial Mortgage Backed Securities Fixed Rate [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 18.6us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_CommercialMortgageBackedSecuritiesFixedRateMember
     
Super Senior | Commercial Mortgage Backed Securities Floating Rate [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_CommercialMortgageBackedSecuritiesFloatingRateMember
     
Super Senior | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 49.3us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
     
Super Senior | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 18.6us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SuperSeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember
     
Senior | Commercial Mortgage Backed Securities Fixed Rate [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 76.2us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_CommercialMortgageBackedSecuritiesFixedRateMember
     
Senior | Commercial Mortgage Backed Securities Floating Rate [Member]        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 0us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= wtm_CommercialMortgageBackedSecuritiesFloatingRateMember
     
Senior | Residential Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments 145.0us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_ResidentialMortgageBackedSecuritiesMember
     
Senior | Commercial Mortgage Backed Securities        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Fair value investments $ 76.2us-gaap_InvestmentsFairValueDisclosure
/ wtm_InvestmentByTrancheLevelsAxis
= wtm_SeniorMember
/ us-gaap_MajorTypesOfDebtAndEquitySecuritiesAxis
= us-gaap_CommercialMortgageBackedSecuritiesMember