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Held for Sale and Discontinued Operations - Financial Statement Disclosure (Details) - USD ($)
$ in Millions
 12 Months Ended
Aug. 01, 2022
Dec. 31, 2023
Dec. 31, 2022
Dec. 31, 2021
Dec. 31, 2018
Dec. 31, 2020
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Disposal Group, Not Discontinued Operation, Gain (Loss) on Disposal, Statement of Income or Comprehensive Income [Extensible Enumeration]     General and administrative expenses General and administrative expenses    
Net income (loss) from discontinued operations, net of tax - NSM Group   $ 0.0 $ 16.4 $ (22.6)    
Net (income) loss from discontinued operations attributable to noncontrolling interests   0.0 (0.7) 1.0    
Total income (loss) from discontinued operations attributable to White Mountains’s common shareholders   0.0 903.2 (3.9)    
Other comprehensive income (loss) from discontinued operations, net of tax - NSM Group   0.0 (5.2) 0.2    
Net gain (loss) from foreign currency translation from sale of discontinued operations, net of tax - NSM Group   0.0 2.9 0.0    
Comprehensive Income (Loss), Net of Tax, Attributable to Noncontrolling Interest   (0.5) 0.9 0.2    
Net Cash Provided by (Used in) Discontinued Operations [Abstract]            
Net cash provided from (used for) operations   0.0 38.7 42.3    
Net cash provided from (used for) investing activities   0.0 7.1 (56.5)    
Net cash used from (used for) financing activities   0.0 (17.5) (1.0)    
Cash balances at beginning of period (includes restricted cash of $89.2 and $78.4 )   0.0 111.6 126.6    
Cash balances at end of period (includes restricted cash of $0.0 and $89.2)   0.0 0.0 111.6    
NSM            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Net gain (loss) from sale of discontinued operations, net of tax   0.0 886.8 0.0    
Sirius Group            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Net gain (loss) from sale of discontinued operations, net of tax   0.0 0.0 18.7    
Discontinued Operations, Disposed of by Sale | NSM            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Total revenues - NSM Group     225.0 330.4    
General and administrative expenses $ 14.0   126.8 190.4    
Broker commission expenses     52.9 80.2    
Change in fair value of contingent consideration     0.1 1.0    
Amortization of other intangible assets     9.1 35.2    
Loss on assets held for sale     0.0 28.7    
Interest expense     12.1 23.3    
Total expenses - NSM Group     201.0 358.8    
Pre-tax income (loss) from discontinued operations - NSM Group     24.0 (28.4)    
Income tax (expense) benefit     (7.6) 5.8    
Net income (loss) from discontinued operations, net tax - NSM Group     16.4 (22.6)    
Net gain (loss) from sale of discontinued operations, net of tax 886.8   886.8 0.0    
Net income (loss) from discontinued operations, net of tax - NSM Group     903.2 (3.9)    
Net (income) loss from discontinued operations attributable to noncontrolling interests     (0.7) 1.0    
Total income (loss) from discontinued operations attributable to White Mountains’s common shareholders     902.5 (2.9)    
Other comprehensive income (loss) from discontinued operations, net of tax - NSM Group     (5.2) 0.2    
Net gain (loss) from foreign currency translation from sale of discontinued operations, net of tax - NSM Group $ 2.9   2.9 0.0    
Comprehensive income (loss) attributable to White Mountains’s common shareholders     900.2 (2.7)    
Comprehensive Income (Loss), Net of Tax, Attributable to Noncontrolling Interest     0.2 (0.1)    
Comprehensive income (loss) attributable to White Mountains’s common shareholders     900.4 (2.8)    
Net Cash Provided by (Used in) Discontinued Operations [Abstract]            
Net cash provided from (used for) operations     38.7 42.3    
Net cash provided from (used for) investing activities     7.1 (56.5)    
Net cash used from (used for) financing activities     (17.5) (1.0)    
Effect of exchange rate changes on cash     4.0 0.2    
Net change in cash during the period     32.3 (15.0)    
Cash balances at beginning of period (includes restricted cash of $89.2 and $78.4 )   $ 0.0 111.6 126.6    
Restricted cash balance     0.0 89.2   $ 78.4
Cash sold as part of the sale of NSM Group (includes restricted cash of $105.1 and $0.0)     (143.9) 0.0    
Restricted cash     105.1 0.0    
Cash balances at end of period (includes restricted cash of $0.0 and $89.2)     0.0 111.6    
Interest paid     (12.0) (16.6)    
Net income tax payments     0.0 0.0    
Discontinued Operations, Disposed of by Sale | NSM | Commission revenues            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Total revenues - NSM Group     176.9 258.0    
Discontinued Operations, Disposed of by Sale | NSM | Other revenues            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Total revenues - NSM Group     48.1 72.4    
Discontinued Operations, Disposed of by Sale | Sirius Group            
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract]            
Net gain (loss) from sale of discontinued operations, net of tax       17.6 $ (17.3)  
Net gain (loss) from sale of discontinued operations, net of tax     $ 0.0 $ 18.7