Investment Securities - Investment Gains and Losses For Level 3 (Details) - USD ($) $ in Millions	12 Months Ended
Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Investment securities
Unrealized investment gains (losses)	$ (313.4)	$ (395.2)	$ 529.7
Proceeds from sale and maturity of investments	500.0	800.0	1,400.0
Level 3
Investment securities
Unrealized investment gains	$ 56.5	$ 98.9	276.0
MediaAlpha
Investment securities
Unrealized investment gains (losses)			$ 278.7

Amount of unrealized gain (loss) on investment in debt security measured at fair value with change in fair value recognized in net income (trading).

Reference 1: http://www.xbrl.org/2009/role/commonPracticeRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 320
-SubTopic 10
-Section 50
-Paragraph 9
-Subparagraph (e)
-URI https://asc.fasb.org/extlink&oid=126970911&loc=d3e27357-111563

+ Details

Name:	us-gaap_DebtSecuritiesTradingUnrealizedGainLoss
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	credit
Period Type:	duration

- Definition

The cash inflow from sales, maturities, prepayments, calls and collections of all investments, including securities and other assets, having ready marketability and intended by management to be liquidated, if necessary, beyond the current operating cycle.

+ References

Reference 1: http://www.xbrl.org/2009/role/commonPracticeRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 230
-SubTopic 10
-Section 45
-Paragraph 12
-URI https://asc.fasb.org/extlink&oid=126954810&loc=d3e3179-108585

+ Details

Name:	us-gaap_ProceedsFromSaleMaturityAndCollectionOfLongtermInvestments
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	debit
Period Type:	duration

- Definition

Line items represent financial concepts included in a table. These concepts are used to disclose reportable information associated with domain members defined in one or many axes to the table.

+ References

No definition available.

+ Details

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

- Definition

Amount of unrealized gain (loss) on investment.

+ References

Reference 1: http://fasb.org/us-gaap/role/ref/legacyRef
-Publisher FASB
-Name Accounting Standards Codification
-Topic 230
-SubTopic 10
-Section 45
-Paragraph 28
-Subparagraph (b)
-URI https://asc.fasb.org/extlink&oid=126954810&loc=d3e3602-108585

+ Details

Name:	us-gaap_UnrealizedGainLossOnInvestments
Namespace Prefix:	us-gaap_
Data Type:	xbrli:monetaryItemType
Balance Type:	credit
Period Type:	duration

- Details

Name:	us-gaap_FairValueByFairValueHierarchyLevelAxis=us-gaap_FairValueInputsLevel3Member
Namespace Prefix:
Data Type:	na
Balance Type:
Period Type:

- Details

Name:	srt_OwnershipAxis=wtm_MediaAlphaMember
Namespace Prefix:
Data Type:	na
Balance Type:
Period Type: