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CONSOLIDATED STATEMENTS OF OPERATIONS - USD ($)
$ in Millions
 3 Months Ended 10 Months Ended 12 Months Ended
Dec. 31, 2020
Sep. 30, 2020
Jun. 30, 2020
Mar. 31, 2020
Dec. 31, 2019
Sep. 30, 2019
Jun. 30, 2019
Mar. 31, 2019
Dec. 31, 2019
Dec. 31, 2020
Dec. 31, 2019
Dec. 31, 2018
Revenues:                        
Earned insurance premiums                   $ 22.8 $ 16.3 $ 13.9
Net investment income                   131.0 79.7 59.0
Net realized and unrealized investment gains (losses)                   30.8 253.2 (108.3)
Net realized and unrealized investment gains from MediaAlpha                   716.8 433.2 (108.3)
Realized gain from the 2019 MediaAlpha Transaction                     67.5  
Commission revenues                   240.8 249.1 389.2
Other revenues                   69.3 47.6 15.3
Total revenues $ 520.8 $ 459.5 $ 259.6 $ (59.2) $ 175.3 $ 155.5 $ 129.0 $ 433.6   1,180.7 893.4 369.1
Expenses:                        
Insurance acquisition expenses                   7.0 5.7 5.3
Other underwriting expenses                   0.4 0.4 0.4
Cost of sales                   11.3 48.1 248.7
General and administrative expenses                   387.0 327.8 233.5
Broker commission expense                   75.3 64.8 28.4
Change in fair value of contingent consideration earnout liabilities                   (3.3) 2.1 2.7
Amortization of other intangible assets                   28.3 21.8 18.8
Interest expense                   29.5 17.6 9.5
Total expenses 163.5 138.3 126.9 106.8 118.8 104.4 113.2 151.9   535.5 488.3 547.3
Pre-tax income (loss) from continuing operations 357.3 321.2 132.7 (166.0) 56.5 51.1 15.8 281.7   645.2 405.1 (178.2)
Income tax benefit (expense) 117.6 (98.5) (24.1) 25.5 (10.4) (8.8) 0.1 (10.2)   20.5 (29.3) 4.0
Net income (loss) from continuing operations 474.9 222.7 108.6 (140.5) 46.1 42.3 15.9 271.5   665.7 375.8 (174.2)
(Loss) gain from sale of Sirius Group, net of tax                   (2.3) 0.8 (17.2)
Net income (loss)                   663.4 376.6 (191.4)
Net loss attributable to non-controlling interests 15.8 10.9 7.8 10.8 15.6 5.5 4.6 12.2   45.3 37.9 50.2
Net income (loss) attributable to White Mountains’s common shareholders $ 489.2 $ 232.9 $ 115.4 $ (128.8) $ 60.9 $ 48.7 $ 20.5 $ 284.4   708.7 414.5 (141.2)
MediaAlpha                        
Revenues:                        
Net investment income                   95.0 14.8 3.7
Net realized and unrealized investment gains from MediaAlpha                   686.0 180.0 0.0
Total revenues                 $ 359.2      
Kudu                        
Revenues:                        
Earned insurance premiums                   0.0 0.0  
Net investment income                   29.5 14.7 0.0
Net realized and unrealized investment gains (losses)                   15.9 6.3 0.0
Realized gain from the 2019 MediaAlpha Transaction                      
Commission revenues                   0.0 0.0  
Other revenues                   0.3 0.2 0.0
Total revenues                   45.7 21.2 0.0
Expenses:                        
Insurance acquisition expenses                   0.0 0.0  
Other underwriting expenses                   0.0 0.0  
Cost of sales                   0.0 0.0  
General and administrative expenses                   11.8 10.1 0.0
Broker commission expense                   0.0 0.0  
Change in fair value of contingent consideration earnout liabilities                   0.0 0.0  
Amortization of other intangible assets                   0.3 0.2 0.0
Interest expense                   6.0 0.1 0.0
Total expenses                   18.1 10.4 0.0
Pre-tax income (loss) from continuing operations                   27.6 10.8  
Kudu | MediaAlpha                        
Revenues:                        
Net realized and unrealized investment gains from MediaAlpha                   0.0 0.0  
HG Global-BAM                        
Revenues:                        
Earned insurance premiums                   22.8 16.3 13.9
Net investment income                   19.5 21.6 16.7
Net realized and unrealized investment gains (losses)                   23.7 27.1 (7.5)
Realized gain from the 2019 MediaAlpha Transaction                     0.0  
Commission revenues                   0.0 0.0 0.0
Other revenues                   2.5 1.6 1.2
Total revenues                   68.5 66.6 24.3
Expenses:                        
Insurance acquisition expenses                   7.0 5.7 5.3
Other underwriting expenses                   0.4 0.4 0.4
Cost of sales                   0.0 0.0 0.0
General and administrative expenses                   56.4 50.5 48.0
Broker commission expense                   0.0 0.0 0.0
Change in fair value of contingent consideration earnout liabilities                   0.0 0.0 0.0
Amortization of other intangible assets                   0.0 0.0 0.0
Interest expense                   0.0 0.0 0.0
Total expenses                   63.8 56.6 53.7
Pre-tax income (loss) from continuing operations                   4.7 10.0 (29.4)
HG Global-BAM | MediaAlpha                        
Revenues:                        
Net realized and unrealized investment gains from MediaAlpha                   0.0 0.0  
NSM                        
Revenues:                        
Earned insurance premiums                   0.0 0.0 0.0
Net investment income                   0.0 0.0 0.0
Net realized and unrealized investment gains (losses)                   0.0 0.0 0.0
Realized gain from the 2019 MediaAlpha Transaction                     0.0  
Commission revenues                   232.5 193.4 89.6
Other revenues                   52.6 39.7 12.0
Total revenues                   285.1 233.1 101.6
Expenses:                        
Insurance acquisition expenses                   0.0 0.0 0.0
Other underwriting expenses                   0.0 0.0 0.0
Cost of sales                   0.0 0.0 0.0
General and administrative expenses                   176.9 132.2 59.4
Broker commission expense                   75.3 64.8 28.4
Change in fair value of contingent consideration earnout liabilities                   (3.3) 2.1 2.7
Amortization of other intangible assets                   26.7 19.4 8.3
Interest expense                   22.1 16.7 8.0
Total expenses                   297.7 235.2 106.8
Pre-tax income (loss) from continuing operations                   (12.6) (2.1) (5.2)
NSM | MediaAlpha                        
Revenues:                        
Net realized and unrealized investment gains from MediaAlpha                   0.0 0.0  
Other Operations                        
Revenues:                        
Earned insurance premiums                   0.0 0.0 0.0
Net investment income                   82.0 43.4 42.3
Net realized and unrealized investment gains (losses)                   (8.8) 219.8 (100.8)
Net realized and unrealized investment gains from MediaAlpha                       0.0
Realized gain from the 2019 MediaAlpha Transaction                   0.0 67.5 0.0
Commission revenues                   8.3 6.9 4.1
Other revenues                   13.9 6.1 0.5
Total revenues                   781.4 523.7 (53.9)
Expenses:                        
Insurance acquisition expenses                   0.0 0.0 0.0
Other underwriting expenses                   0.0 0.0 0.0
Cost of sales                   11.3 7.5 3.7
General and administrative expenses                   141.9 122.5 94.4
Broker commission expense                   0.0 0.0 0.0
Change in fair value of contingent consideration earnout liabilities                   0.0 0.0 0.0
Amortization of other intangible assets                   1.3 0.6 0.2
Interest expense                   1.4 0.6 0.3
Total expenses                   155.9 131.2 98.6
Pre-tax income (loss) from continuing operations                   625.5 392.5 (152.5)
Other Operations | MediaAlpha                        
Revenues:                        
Net realized and unrealized investment gains from MediaAlpha                   686.0 180.0  
MediaAlpha                        
Revenues:                        
Earned insurance premiums                     0.0 0.0
Net investment income                     0.0 0.0
Net realized and unrealized investment gains (losses)                     0.0 0.0
Realized gain from the 2019 MediaAlpha Transaction                     0.0  
Commission revenues                   0.0 48.8 295.5
Other revenues                   0.0 0.0 1.6
Total revenues                   0.0 48.8 297.1
Expenses:                        
Insurance acquisition expenses                     0.0 0.0
Other underwriting expenses                     0.0 0.0
Cost of sales                   0.0 40.6 245.0
General and administrative expenses                   0.0 12.5 31.7
Broker commission expense                     0.0 0.0
Change in fair value of contingent consideration earnout liabilities                     0.0 0.0
Amortization of other intangible assets                   0.0 1.6 10.3
Interest expense                   0.0 0.2 1.2
Total expenses                   $ 0.0 54.9 288.2
Pre-tax income (loss) from continuing operations                     (6.1) $ 8.9
MediaAlpha | MediaAlpha                        
Revenues:                        
Net realized and unrealized investment gains from MediaAlpha                     $ 0.0