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SCHEDULE II CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT - Statement of Cash Flows (Details) - USD ($)
$ in Millions
 3 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, 2020
Dec. 31, 2019
Dec. 31, 2018
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
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)
Adjustments to reconcile net income to net cash used for operations:                      
Net realized and unrealized investment (gains) losses                 (716.8) (433.2) 108.3
Net income from discontinued operations, net of tax 1.5 $ 0.7 $ 1.0 (0.9) 0.8 $ (0.9) $ 0.0 (0.7)      
Net change in other assets and liabilities, net                 30.9 20.4 (38.8)
Net cash used for operations                 (60.6) (120.5) (31.1)
Cash flows from investing activities:                      
Net decrease in short-term investments                 58.7 21.9 (39.0)
Net cash provided from (used for) investing activities                 64.6 (59.9) 459.2
Cash flows from financing activities:                      
Repurchases and retirement of common shares                 (78.5) 0.0 (511.9)
Dividends paid on common shares                 (3.2) (3.2) (3.8)
Net cash provided from (used for) financing activities                 49.0 230.5 (414.3)
Net (decrease) increase in cash during the year                 50.2 50.7 13.2
Cash balance at beginning of year       161.0       110.3 161.0 110.3 97.1
Cash balance at end of year 211.2       161.0       211.2 161.0 110.3
Amortization of restricted share awards                 16.6 10.5 13.0
Payable to subsidiary (4.8)       (6.6)       (4.8) (6.6) (4.0)
White Mountains Insurance Group Ltd.                      
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Net income (loss) attributable to White Mountains’s common shareholders                 708.7 414.5 (141.2)
Adjustments to reconcile net income to net cash used for operations:                      
Net realized and unrealized investment (gains) losses                 10.1 (61.0) 57.8
Undistributed earnings from subsidiaries                 (782.0) (398.5) 27.4
Net income from discontinued operations, net of tax                 2.3 (0.8) 17.2
Other non-cash reconciling items, primarily amortization of restricted shares and option awards                 19.0 20.0 34.6
Net change in other assets and liabilities, net                 (2.6) 3.0 16.7
Net cash used for operations                 (44.5) (22.8) 12.5
Cash flows from investing activities:                      
Net decrease in short-term investments                 (127.4) (37.6) 134.0
Purchases of investment securities                 (6.7) (14.8) (321.2)
Sales and maturities of investment securities                 189.7 207.9 967.6
Issuance of debt (to) from subsidiaries                 (44.5) (83.5) (55.2)
Repayment of debt to (from) subsidiaries                 92.6 5.0 31.0
Net (contributions to) distributions from subsidiaries                 29.1 (46.1) (258.2)
Net cash provided from (used for) investing activities                 132.8 30.9 498.0
Cash flows from financing activities:                      
Repurchases and retirement of common shares                 (78.5) 0.0 (510.9)
Dividends paid on common shares                 (3.2) (3.2) (3.8)
Payments of restricted shares withholding taxes                 (6.6) (4.9) (10.0)
Net cash provided from (used for) financing activities                 (88.3) (8.1) (524.7)
Net (decrease) increase in cash during the year                 0.0 0.0 (14.2)
Cash balance at beginning of year       $ 0.7       $ 0.7 0.7 0.7 14.9
Cash balance at end of year 0.7       0.7       0.7 0.7 0.7
Payable to subsidiary $ 195.6       $ 69.3       195.6 69.3  
Bridge Holdings, Ltd. | White Mountains Insurance Group Ltd.                      
Cash flows from investing activities:                      
Net (contributions to) distributions from subsidiaries                     255.3
Cash flows from financing activities:                      
Transfer to investments                   70.5 (22.7)
White Mountains Investment, Ltd. | White Mountains Insurance Group Ltd.                      
Cash flows from investing activities:                      
Net (contributions to) distributions from subsidiaries                     2.9
Cash flows from financing activities:                      
Transfer to investments                   2.0  
Transfer from investments                 6.8 24.4  
HG Global | White Mountains Insurance Group Ltd.                      
Cash flows from financing activities:                      
Transfer from investments                 22.3 1.9  
Non-cash reconciling item | Guilford Holdings, Inc.                      
Cash flows from financing activities:                      
Transfer to investments                 (169.6)   (349.5)
Noncash Total | White Mountains Insurance Group Ltd.                      
Cash flows from financing activities:                      
Transfer to investments                     603.9
Transfer from investments                     1,065.4
Fixed maturity investments | White Mountains Insurance Group Ltd.                      
Cash flows from financing activities:                      
Transfer to investments                     170.5
Transfer from investments                     373.4
Fixed maturity investments | Guilford Holdings, Inc.                      
Cash flows from financing activities:                      
Transfer from investments                     170.4
Equity Securities | White Mountains Insurance Group Ltd.                      
Cash flows from financing activities:                      
Transfer to investments                     148.8
Transfer from investments                     490.1
Other long-term investments | White Mountains Insurance Group Ltd.                      
Cash flows from financing activities:                      
Transfer to investments                     22.7
Transfer from investments                     22.7
Short-term investments | White Mountains Insurance Group Ltd.                      
Cash flows from financing activities:                      
Transfer to investments                 169.6   284.6
Transfer from investments                     179.2
Short-term investments | Guilford Holdings, Inc.                      
Cash flows from financing activities:                      
Transfer from investments                     179.2
Bridge Holdings, Ltd. | Guilford Holdings, Inc.                      
Cash flows from financing activities:                      
Transfer to investments                     (350.0)
Bridge Holdings, Ltd. | White Mountains Investment, Ltd.                      
Cash flows from financing activities:                      
Transfer to investments                     (1.0)
Swedish Tax Authority | Sirius Group                      
Cash flows from financing activities:                      
Loss contingency accrual, period increase (decrease)                 (2.3) $ 0.8 $ (17.3)
Swedish Tax Authority | Sirius Group | Sirius Group                      
Cash flows from financing activities:                      
Loss contingency accrual, period increase (decrease)                 $ 2.2