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Segment Information - Financial Information for White Mountain's Segments (Details) - USD ($)
$ in Millions
 3 Months Ended
Mar. 31, 2021
Mar. 31, 2020
Segment Reporting Information [Line Items]    
Earned insurance premiums $ 111.0 $ 5.4
Net investment income 20.6 22.9
Net realized and unrealized investment (losses) gains 1.1 (186.7)
Net realized and unrealized investment (losses) gains from investment in MediaAlpha (40.6) (156.7)
Commission revenues 61.9 55.1
Other revenues 25.3 14.1
Total revenues 178.2 (59.2)
Loss and loss adjustment expenses 66.0  
Insurance and reinsurance acquisition expenses 38.6  
Cost of sales 4.0 2.0
General and administrative expenses 138.4 74.3
Loss on assets held for sale 28.7  
Broker commission expenses 18.9 18.3
Change in fair value of contingent consideration earnout liabilities 0.0 (0.6)
Amortization of other intangible assets 9.2 5.1
Interest expense 13.1 6.0
Total expenses 316.9 106.8
Pre-tax loss from continuing operations (138.7) (166.0)
Marketing Technology (MediaAlpha)    
Segment Reporting Information [Line Items]    
Net realized and unrealized investment (losses) gains from investment in MediaAlpha (41.7) 30.0
HG Global/ BAM    
Segment Reporting Information [Line Items]    
Earned insurance premiums 6.4 5.4
Net investment income 4.5 5.5
Net realized and unrealized investment (losses) gains (17.9) 6.1
Commission revenues 0.0 0.0
Other revenues 0.3 0.5
Total revenues (6.7) 17.5
Loss and loss adjustment expenses 0.0  
Insurance and reinsurance acquisition expenses 1.9  
Cost of sales 0.0 0.0
General and administrative expenses 16.4 14.7
Loss on assets held for sale 0.0  
Broker commission expenses 0.0 0.0
Change in fair value of contingent consideration earnout liabilities 0.0 0.0
Amortization of other intangible assets 0.0 0.0
Interest expense 0.0 0.0
Total expenses 18.3 16.4
Pre-tax loss from continuing operations (25.0) 1.1
HG Global/ BAM | Marketing Technology (MediaAlpha)    
Segment Reporting Information [Line Items]    
Net realized and unrealized investment (losses) gains from investment in MediaAlpha 0.0 0.0
Ark    
Segment Reporting Information [Line Items]    
Earned insurance premiums 104.6 0.0
Net investment income 0.8 0.0
Net realized and unrealized investment (losses) gains 1.1 0.0
Commission revenues 0.0  
Other revenues 2.6 0.0
Total revenues 109.1 0.0
Loss and loss adjustment expenses 66.0 0.0
Insurance and reinsurance acquisition expenses 36.7 0.0
Cost of sales 0.0  
General and administrative expenses 26.6 0.0
Loss on assets held for sale 0.0  
Broker commission expenses 0.0  
Change in fair value of contingent consideration earnout liabilities 0.0  
Amortization of other intangible assets 0.0  
Interest expense 1.1 0.0
Total expenses 141.6 0.0
Pre-tax loss from continuing operations (32.5)  
Ark | General and administrative expenses, including underwriting expense    
Segment Reporting Information [Line Items]    
General and administrative expenses 37.8  
Ark | Marketing Technology (MediaAlpha)    
Segment Reporting Information [Line Items]    
Net realized and unrealized investment (losses) gains from investment in MediaAlpha 0.0  
NSM    
Segment Reporting Information [Line Items]    
Earned insurance premiums 0.0 0.0
Net investment income 0.0 0.0
Net realized and unrealized investment (losses) gains 0.0 0.0
Commission revenues 59.6 53.0
Other revenues 15.2 12.0
Total revenues 74.8 65.0
Loss and loss adjustment expenses 0.0  
Insurance and reinsurance acquisition expenses 0.0  
Cost of sales 0.0 0.0
General and administrative expenses 46.0 39.6
Loss on assets held for sale 28.7 0.0
Broker commission expenses 18.9 18.3
Change in fair value of contingent consideration earnout liabilities 0.0 (0.6)
Amortization of other intangible assets 8.6 4.8
Interest expense 5.9 4.3
Total expenses 108.1 66.4
Pre-tax loss from continuing operations (33.3) (1.4)
NSM | Marketing Technology (MediaAlpha)    
Segment Reporting Information [Line Items]    
Net realized and unrealized investment (losses) gains from investment in MediaAlpha 0.0 0.0
Kudu    
Segment Reporting Information [Line Items]    
Earned insurance premiums 0.0 0.0
Net investment income 8.2 7.3
Net realized and unrealized investment (losses) gains 15.8 (24.8)
Commission revenues 0.0 0.0
Other revenues 0.1 0.1
Total revenues 24.1 (17.4)
Loss and loss adjustment expenses 0.0  
Insurance and reinsurance acquisition expenses 0.0  
Cost of sales 0.0 0.0
General and administrative expenses 2.5 2.5
Loss on assets held for sale 0.0  
Broker commission expenses 0.0 0.0
Change in fair value of contingent consideration earnout liabilities 0.0 0.0
Amortization of other intangible assets 0.1 0.1
Interest expense 5.8 1.4
Total expenses 8.4 4.0
Pre-tax loss from continuing operations 15.7 (21.4)
Kudu | Marketing Technology (MediaAlpha)    
Segment Reporting Information [Line Items]    
Net realized and unrealized investment (losses) gains from investment in MediaAlpha 0.0 0.0
Other Operations    
Segment Reporting Information [Line Items]    
Earned insurance premiums 0.0 0.0
Net investment income 7.1 10.1
Net realized and unrealized investment (losses) gains 2.1 (168.0)
Commission revenues 2.3 2.1
Other revenues 7.1 1.5
Total revenues (23.1) (124.3)
Loss and loss adjustment expenses 0.0  
Insurance and reinsurance acquisition expenses 0.0  
Cost of sales 4.0 2.0
General and administrative expenses 35.7 17.5
Loss on assets held for sale 0.0  
Broker commission expenses 0.0 0.0
Change in fair value of contingent consideration earnout liabilities 0.0 0.0
Amortization of other intangible assets 0.5 0.2
Interest expense 0.3 0.3
Total expenses 40.5 20.0
Pre-tax loss from continuing operations (63.6) (144.3)
Other Operations | Marketing Technology (MediaAlpha)    
Segment Reporting Information [Line Items]    
Net realized and unrealized investment (losses) gains from investment in MediaAlpha $ (41.7) $ 30.0