Investment Securities - Cost and Amortized Cost Maturity Schedule (Details) $ in Millions	Dec. 31, 2022 USD ($)
Cost or Amortized Cost
Total fixed maturity investments	$ 2,076.0
Carrying Value
Total fixed maturity investments	1,920.9
Fixed Maturities and Convertible Fixed Maturities Excluding Mortgage Backed Securities
Cost or Amortized Cost
Due in one year or less	204.8
Due after one year through five years	914.0
Due after five years through ten years	374.4
Due after ten years	103.3
Carrying Value
Due in one year or less	201.2
Due after one year through five years	853.2
Due after five years through ten years	337.4
Due after ten years	92.0
Mortgage and asset-backed securities
Cost or Amortized Cost
Mortgage and asset-backed securities and collateralized loan obligations	479.5
Carrying Value
Mortgage and asset-backed securities and collateralized loan obligations	$ 437.1

Fair value of investment in debt security measured at amortized cost (held-to-maturity), with single maturity date and allocated without single maturity date, maturing in sixth through tenth fiscal year following current fiscal year. Excludes interim and annual periods when interim periods are reported from current statement of financial position date (rolling approach).

Reference 1: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3A
-Subparagraph (c)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=SL120269850-112803

Reference 2: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)(3)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

Reference 3: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5B
-Subparagraph (c)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=SL120269825-111563

Reference 4: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-Subparagraph (c)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- Definition

Amount, after allowance for credit loss, of investment in debt security measured at amortized cost (held-to-maturity) with single maturity date and allocated without single maturity date, maturing in sixth through tenth fiscal year following current fiscal year. Excludes interim and annual periods when interim periods are reported from current statement of financial position date (rolling approach).

+ References

Reference 1: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)(3)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

Reference 2: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-Subparagraph (c)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesAfterFiveThroughTenYearsNetCarryingAmount
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- Definition

Fair value of investment in debt security measured at amortized cost (held-to-maturity), with single maturity date and allocated without single maturity date, maturing in second through fifth fiscal year following current fiscal year. Excludes interim and annual periods when interim periods are reported from current statement of financial position date (rolling approach).

+ References

Reference 1: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5B
-Subparagraph (b)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=SL120269825-111563

Reference 2: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3A
-Subparagraph (b)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=SL120269850-112803

Reference 3: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)(2)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

Reference 4: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-Subparagraph (b)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- Definition

Amount, after allowance for credit loss, of investment in debt security measured at amortized cost (held-to-maturity) with single maturity date and allocated without single maturity date, maturing in second through fifth fiscal year following current fiscal year. Excludes interim and annual periods when interim periods are reported from current statement of financial position date (rolling approach).

+ References

Reference 1: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)(2)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

Reference 2: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-Subparagraph (b)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesAfterOneThroughFiveYearsNetCarryingAmount
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- Definition

Fair value of investment in debt security measured at amortized cost (held-to-maturity), with single maturity date and allocated without single maturity date, maturing after tenth fiscal year following current fiscal year. Excludes interim and annual periods when interim periods are reported from current statement of financial position date (rolling approach).

+ References

Reference 1: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3A
-Subparagraph (d)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=SL120269850-112803

Reference 2: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)(4)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

Reference 3: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-Subparagraph (d)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

Reference 4: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5B
-Subparagraph (d)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=SL120269825-111563

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesAfterTenYearsFairValue
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- Definition

Amount, after allowance for credit loss, of investment in debt security measured at amortized cost (held-to-maturity) with single maturity date and allocated without single maturity date, maturing after tenth fiscal year following current fiscal year. Excludes interim and annual periods when interim periods are reported from current statement of financial position date (rolling approach).

+ References

Reference 1: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)(4)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

Reference 2: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-Subparagraph (d)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesAfterTenYearsNetCarryingAmount
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- Definition

Amount, after allowance for credit loss, of investment in debt security measured at amortized cost (held-to-maturity) with single maturity date and allocated without single maturity date.

+ References

Reference 1: http://www.xbrl.org/2009/role/commonPracticeRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

Reference 2: http://www.xbrl.org/2009/role/commonPracticeRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasis
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- References

No definition available.

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateAmortizedCostBasisAbstract
Namespace Prefix:	us-gaap_
Data Type:	xbrli:stringItemType
Balance Type:	na
Period Type:	duration

- Definition

Fair value of investment in debt security measured at amortized cost (held-to-maturity), with single maturity date and allocated without single maturity date.

+ References

Reference 1: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

Reference 2: http://www.xbrl.org/2009/role/commonPracticeRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3A
-URI https://asc.fasb.org/extlink&oid=126980459&loc=SL120269850-112803

Reference 3: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

Reference 4: http://www.xbrl.org/2009/role/commonPracticeRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5B
-URI https://asc.fasb.org/extlink&oid=126970911&loc=SL120269825-111563

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValue
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- References

No definition available.

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesSingleMaturityDateFairValueAbstract
Namespace Prefix:	us-gaap_
Data Type:	xbrli:stringItemType
Balance Type:	na
Period Type:	duration

- Definition

Fair value of investment in debt security measured at amortized cost (held-to-maturity), with single maturity date and allocated without single maturity date, maturing in next fiscal year following current fiscal year. Excludes interim and annual periods when interim periods are reported from current statement of financial position date (rolling approach).

+ References

Reference 1: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)(1)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

Reference 2: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5B
-Subparagraph (a)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=SL120269825-111563

Reference 3: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3A
-Subparagraph (a)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=SL120269850-112803

Reference 4: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-Subparagraph (a)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesWithinOneYearFairValue
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- Definition

Amount, after allowance for credit loss, of investment in debt security measured at amortized cost (held-to-maturity) with single maturity date and allocated without single maturity date, maturing in next fiscal year following current fiscal year. Excludes interim and annual periods when interim periods are reported from current statement of financial position date (rolling approach).

+ References

Reference 1: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 942
-SubTopic 320
-Section 50
-Paragraph 3
-Subparagraph (a)
-URI https://asc.fasb.org/extlink&oid=126980459&loc=d3e62586-112803

Reference 2: http://www.xbrl.org/2003/role/disclosureRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 5
-Subparagraph (f)(1)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27232-111563

+ Details

Name:	us-gaap_HeldToMaturitySecuritiesDebtMaturitiesWithinOneYearNetCarryingAmount
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	instant

- Definition

Debt Securities, Held-to-Maturity, Amortized Cost, Maturity, Allocated and Single Maturity Date

+ References

No definition available.

+ Details

Name:	wtm_DebtSecuritiesHeldToMaturityAmortizedCostMaturityAllocatedAndSingleMaturityDate
Namespace Prefix:	wtm_
Data Type:	xbrli:monetaryItemType
Balance Type:	credit
Period Type:	instant

- Definition

Debt Securities, Held-to-Maturity, Fair Value, Maturity, Allocated and Single Maturity Date

+ References

No definition available.

+ Details

Name:	wtm_DebtSecuritiesHeldToMaturityFairValueMaturityAllocatedAndSingleMaturityDate
Namespace Prefix:	wtm_
Data Type:	xbrli:monetaryItemType
Balance Type:	credit
Period Type:	instant

- Details

Name:	us-gaap_FinancialInstrumentAxis=wtm_FixedMaturitiesAndConvertibleFixedMaturitiesExcludingMortgageBackedSecuritesAssetBackedSecuritiesAndPreferredStockMember
Namespace Prefix:
Data Type:	na
Balance Type:
Period Type:

- Details

Name:	us-gaap_FinancialInstrumentAxis=us-gaap_AssetBackedSecuritiesMember
Namespace Prefix:
Data Type:	na
Balance Type:
Period Type: