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Held for Sale and Discontinued Operations - Financial Statement Disclosure (Details) - USD ($)
$ in Millions
 3 Months Ended
Mar. 31, 2023
Mar. 31, 2022
Dec. 31, 2022
Dec. 31, 2021
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]        
Net income (loss) from discontinued operations, net of tax $ 0.0 $ 3.7    
Net (income) loss from discontinued operations attributable to noncontrolling interests 0.0 (0.1)    
Other comprehensive income (loss) from discontinued operations, net of tax - NSM Group 0.0 (1.9)    
Net Cash Provided by (Used in) Discontinued Operations [Abstract]        
Net cash provided from (used for) operations 0.0 4.4    
Net cash provided from (used for) investing activities 0.0 7.3    
Net cash used from (used for) financing activities 0.0 (10.3)    
Net change in cash during the period (52.3) 65.8    
Cash balances at beginning of period (includes restricted cash balances of $12.2 and $4.5 and excludes discontinued operations cash balances of $0.0 and $111.6) 255.0 147.7    
Cash balances at end of period (includes restricted cash balances of $13.0 and $4.5 and excludes discontinued operations cash balances of $0.0 and $113.6) 202.7 213.5    
Restricted cash balance 13.0 4.5 $ 12.2 $ 4.5
Interest paid (5.8) (5.5)    
Net income tax payments 17.8 0.3    
Discontinued Operations, Held-for-sale | NSM Insurance Group        
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]        
Commission revenues   70.1    
Other revenues   18.4    
Total revenues   88.5    
General and administrative expenses   54.0    
Broker commission expenses   20.6    
Change in fair value of contingent consideration   0.1    
Amortization of other intangible assets   9.1    
Interest expense   2.1    
Total expenses   85.9    
Pre-tax income (loss) from discontinued operations   2.6    
Income tax (expense) benefit   1.1    
Net income (loss) from discontinued operations, net of tax   3.7    
Net (income) loss from discontinued operations attributable to noncontrolling interests   (0.1)    
Total income (loss) from discontinued operations attributable to White Mountains’s common shareholders   3.6    
Other comprehensive income (loss) from discontinued operations, net of tax - NSM Group   (1.9)    
Comprehensive income (loss) from discontinued operations   1.7    
Other comprehensive income (loss) from discontinued operations attributable to noncontrolling interests   0.1    
Comprehensive income (loss) from discontinued operations attributable to White Mountains’s common shareholders   1.8    
Net Cash Provided by (Used in) Discontinued Operations [Abstract]        
Net cash provided from (used for) operations   4.4    
Net cash provided from (used for) investing activities   7.3    
Net cash used from (used for) financing activities   (10.3)    
Effect of exchange rate changes on cash   0.6    
Net change in cash during the period   2.0    
Cash balances at beginning of period (includes restricted cash balances of $12.2 and $4.5 and excludes discontinued operations cash balances of $0.0 and $111.6) 0.0 111.6    
Cash balances at end of period (includes restricted cash balances of $13.0 and $4.5 and excludes discontinued operations cash balances of $0.0 and $113.6) $ 0.0 113.6    
Restricted cash balance   90.2   $ 89.2
Interest paid   (2.9)    
Net income tax payments   $ 0.0