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SCHEDULE II - CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT - CONDENSED STATEMENTS OF CASH FLOWS (Details) - USD ($) $ in Millions | 12 Months Ended
--- | ---
Dec. 31, 2023 | Dec. 31, 2022 | Dec. 31, 2021
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT |  |  |
Net income (loss) | $ 580.9 | $ 712.4 | $ (321.9)
Charges (credits) to reconcile net income to net cash from operations: |  |  |
Net realized and unrealized investment (gains) losses | (434.2) | 191.5 | 246.1
Net (income) loss from discontinued operation, net of tax - NSM Group |  | (902.5) | 2.9
Net other operating activities | (3.9) | 80.8 | 10.7
Net cash provided from (used for) operations | 404.1 | 365.0 | 38.6
Cash flows from investing activities: |  |  |
Net change in short-term investments | (495.8) | (455.1) | 59.8
Release of cash (pre-funding) for ILS funds managed by Elementum | 70.0 | (70.0) | 0.0
Proceeds from the sale of business, net of cash sold | 17.3 | 1,392.0 | 0.0
Cash sold in subsidiary transaction | 0.8 | 144.4 | 0.0
Net cash provided from (used for) investing activities | (543.9) | 115.5 | (208.3)
Cash flows from financing activities: |  |  |
Repurchases and retirement of common shares | (32.7) | (615.8) | (107.5)
Cash dividends paid to common shareholders | (2.6) | (3.0) | (3.1)
Net cash provided from (used for) financing activities – continuing operations | 7.2 | (344.9) | 217.6
Cash balance at beginning of year | 255.0 | 147.7 | 84.6
Cash balance at end of year | 122.4 | 255.0 | 147.7
Amortization of restricted share awards | 15.3 | 14.0 | 14.7
Total White Mountains’s common shareholders’ equity | 4,240.5 | 3,746.9 |
Common equity securities, at fair value | 538.4 | 668.4 |
Other long-term investments | 1,998.2 | 1,488.0 |
Net change in (receivables) payables to subsidiaries | 8.4 | 3.3 | (6.5)
WM Lincoln |  |  |
Cash flows from financing activities: |  |  |
Investments in consolidated subsidiaries |  |  | 212.6
White Mountains Insurance Group Ltd. |  |  |
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT |  |  |
Net income (loss) | 509.2 | 792.8 | (275.4)
Charges (credits) to reconcile net income to net cash from operations: |  |  |
Net realized and unrealized investment (gains) losses | (78.9) | 5.6 | 0.1
Equity in (earnings) losses from consolidated and unconsolidated subsidiaries, net of tax | (489.2) | 42.0 | 232.3
Net (income) loss from discontinued operation, net of tax - NSM Group | 0.0 | (16.4) | 22.6
Other non-cash reconciling items | 12.7 | 7.0 | 16.6
Accumulated earnings distributed from subsidiary in cash | 17.3 | 7.0 | 0.0
Net other operating activities | 9.2 | 17.2 | (5.7)
Net cash provided from (used for) operations | (19.7) | (31.6) | (28.2)
Cash flows from investing activities: |  |  |
Net change in short-term investments | (63.8) | 1,165.6 | 17.7
Purchases of investment securities | (125.0) | (359.2) | 0.0
Sales and maturities of investment securities | 335.4 | 15.7 | 0.0
Purchases of investment securities from subsidiaries | 0.0 | (14.0) | (26.4)
Sales of investment securities to subsidiaries | 0.0 | 0.0 | 36.4
Release of cash (pre-funding) for ILS funds managed by Elementum | 70.0 | (70.0) | 0.0
Net issuance of debt (to) from subsidiaries | (132.5) | (142.0) | 94.0
Net repayment of debt to (from) subsidiaries | 31.4 | (15.0) | 0.0
Net distributions from (contributions to) subsidiaries | (60.3) | 49.3 | 17.0
Proceeds from the sale of business, net of cash sold | 0.0 | 19.5 | 0.0
Cash sold in subsidiary transaction | 0.0 | 0.5 | 0.0
Net cash provided from (used for) investing activities | 55.2 | 649.9 | 138.7
Cash flows from financing activities: |  |  |
Repurchases and retirement of common shares | (32.7) | (615.8) | (107.5)
Cash dividends paid to common shareholders | (2.6) | (3.0) | (3.1)
Net cash provided from (used for) financing activities – continuing operations | (35.3) | (618.8) | (110.6)
Net change in cash during the year | 0.2 | (0.5) | (0.1)
Cash balance at beginning of year | 0.1 | 0.6 | 0.7
Cash balance at end of year | 0.3 | 0.1 | 0.6
Total White Mountains’s common shareholders’ equity | 4,240.5 | 3,746.9 |
Investments in consolidated subsidiaries | 3,666.9 | 3,027.2 |
Fixed maturity investments, at fair value | 0.0 | 49.2 |
Common equity securities, at fair value | 147.8 | 342.8 |
Other long-term investments | 160.5 | 49.3 |
Short-term investments, at fair value | 198.8 | 105.2 |
Other assets | 4.0 | 75.3 |
Noncash payment in short-term investments | 10.0 |  |
Subsidiary - Bridge Holdings, Ltd. |  |  |
Charges (credits) to reconcile net income to net cash from operations: |  |  |
Accumulated earnings distributed from subsidiary in cash |  | 7.0 |
Cash flows from financing activities: |  |  |
Repayments of principal debt |  | 15.0 |
Contributions |  |  | 12.6
Contributions, short-term investments and cash |  |  | 18.0
Contributions, short-term investments |  |  | 17.9
Contributions, cash |  |  | 0.1
Subsidiary - White Mountain Adams, Inc. |  |  |
Cash flows from financing activities: |  |  |
Distributions |  |  | 42.7
Distributions, short-term investments |  | 100.0 | 37.1
Distributions, cash |  |  | 5.6
Subsidiary - White Mountains Investments Bermuda |  |  |
Cash flows from financing activities: |  |  |
Contributions |  |  | 19.7
Contributions, short-term investments |  |  | 19.1
Distributions, cash |  | 51.0 |
Subsidiary - HG Global |  |  |
Cash flows from financing activities: |  |  |
Contributions, cash |  | 116.3 |
Proceeds from borrowings |  | 6.0 |
Subsidiary - Ark Insurance Holdings Limited |  |  |
Cash flows from financing activities: |  |  |
Contributions, cash |  | 7.7 |
Subsidiary - PSC Holdings, Ltd. |  |  |
Cash flows from financing activities: |  |  |
Contributions, cash |  | 1.3 |
Subsidiary - White Mountain Hinson Bermuda |  |  |
Cash flows from financing activities: |  |  |
Contributions, cash |  |  | 0.6
Proceeds from borrowings |  | 205.0 |
WM Birkdale |  |  |
Cash flows from financing activities: |  |  |
Repayments of principal debt | 20.5 |  |
Repayments of debt in investments | 73.8 |  |
Repayments of debt in fixed maturity investments | 36.9 |  |
Repayments of debt in short-term investments | 36.9 |  |
Bridge Holdings, Ltd. |  |  |
Cash flows from financing activities: |  |  |
Total White Mountains’s common shareholders’ equity |  | 3,540.6 |
Intercompany note receivable |  | 76.4 |
Investments in consolidated subsidiaries |  | 2,003.6 |
Fixed maturity investments, at fair value |  | 28.6 |
Common equity securities, at fair value |  | 8.1 |
Other long-term investments |  | 52.2 |
Short-term investments, at fair value |  | 1,358.7 |
Other assets |  | 6.0 |
Proceeds from borrowings |  | 69.0 |
Bridge Holdings, Ltd. | White Mountains Insurance Group Ltd. |  |  |
Cash flows from financing activities: |  |  |
Repayments of principal debt |  |  | 200.0
WM Hinson |  |  |
Cash flows from financing activities: |  |  |
Repayments of principal debt | 42.4 |  |
Proceeds from borrowings | 20.0 |  |
Repayments of debt in investments | 107.6 |  |
Repayments of debt in fixed maturity investments | 45.9 |  |
Repayments of debt in short-term investments | 61.7 |  |
HG Global |  |  |
Cash flows from financing activities: |  |  |
Repayments of principal debt | 9.5 |  |
Proceeds from borrowings | 7.5 |  |
White Mountain Investments Luxembourg |  |  |
Cash flows from financing activities: |  |  |
Proceeds from borrowings | 105.0 |  |
White Mountains Adams, Inc. |  |  |
Cash flows from financing activities: |  |  |
Distributions, cash |  | 25.0 |
NSM |  |  |
Charges (credits) to reconcile net income to net cash from operations: |  |  |
Net (gain) loss from sale of discontinued operations, net of tax | 0.0 | (886.8) | 0.0
NSM | White Mountains Insurance Group Ltd. |  |  |
Charges (credits) to reconcile net income to net cash from operations: |  |  |
Net (gain) loss from sale of discontinued operations, net of tax | 0.0 | (886.8) | 0.0
Sirius Group |  |  |
Charges (credits) to reconcile net income to net cash from operations: |  |  |
Net (gain) loss from sale of discontinued operations, net of tax | 0.0 | 0.0 | (18.7)
Sirius Group | White Mountains Insurance Group Ltd. |  |  |
Charges (credits) to reconcile net income to net cash from operations: |  |  |
Net (gain) loss from sale of discontinued operations, net of tax | $ 0.0 | $ 0.0 | $ (18.7)

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