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SCHEDULE II CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT (Details 3) (USD $)
3 Months Ended 12 Months Ended 1 Months Ended 12 Months Ended 1 Months Ended 12 Months Ended
Dec. 31, 2013
Sep. 30, 2013
Jun. 30, 2013
Mar. 31, 2013
Dec. 31, 2012
Sep. 30, 2012
Jun. 30, 2012
Mar. 31, 2012
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Dec. 31, 2010
Dec. 31, 2013
Lone Tree Insurance Group Ltd
Nov. 30, 2011
Lone Tree Insurance Group Ltd
Dec. 31, 2013
White Mountains Insurance Group Ltd.
Dec. 31, 2012
White Mountains Insurance Group Ltd.
Dec. 31, 2011
White Mountains Insurance Group Ltd.
Dec. 31, 2010
White Mountains Insurance Group Ltd.
Dec. 31, 2013
Fixed maturity investments
Lone Tree Insurance Group Ltd
Nov. 30, 2011
Fixed maturity investments
Lone Tree Insurance Group Ltd
Nov. 30, 2011
Short-term investments
Lone Tree Insurance Group Ltd
Dec. 31, 2013
Cash
Lone Tree Insurance Group Ltd
Dec. 31, 2013
Revolving Credit Facility [Member]
White Mountains Insurance Group Ltd.
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                                              
Net income attributable to White Mountains’ common shareholders $ 117,900,000 $ 57,200,000 $ 26,300,000 $ 120,400,000 $ 68,200,000 $ 19,100,000 $ 26,100,000 $ 94,000,000 $ 321,800,000 $ 207,400,000 $ 767,900,000       $ 321,800,000 $ 207,400,000 $ 767,900,000            
Charges (credits) to reconcile net income to net cash (used for) provided from operations:                                              
Net realized and unrealized investment gains                 (161,700,000) (118,200,000) (74,100,000)       (200,000) (11,000,000) (3,100,000)            
Undistributed current earnings from subsidiaries                             (359,700,000) (219,300,000) (806,700,000)            
Other non-cash reconciling items including restricted share and option amortization                             15,600,000 22,100,000 7,200,000            
Net change in other assets and liabilities, net                 63,200,000 (52,700,000) (62,200,000)       (2,900,000) (10,000,000) 6,500,000            
Net cash used for operations                 (101,000,000) (225,800,000) (114,500,000)       (25,400,000) (10,800,000) (28,200,000)            
Cash flows from investing activities:                                              
Net decrease in short-term investments                 34,800,000 145,300,000 174,500,000       7,500,000 [1] 63,300,000 [1] 267,300,000 [1]            
Purchases of investment securities                             (26,200,000) [1],[2] (706,200,000) [1],[2] (237,300,000) [1],[2]            
Sales and maturities of investment securities                 4,924,800,000 6,997,500,000 5,034,000,000       61,100,000 [3] 2,009,700,000 [3] 59,000,000 [3]            
Issuance of debt (to) from subsidiaries                             153,900,000 [4] (121,000,000) [4] 0 [4]            
Repayment of debt (to) from subsidiaries                             (10,300,000) [1] 28,500,000 [1] 192,500,000 [1]            
Payments to subsidiaries                             0 [3] (663,000,000) [3] 0 [3]            
Distributions from subsidiaries                             100,000 [2] 0 [2] 7,200,000 [2]            
Net cash provided from investing activities                 401,800,000 829,600,000 799,600,000       186,100,000 611,300,000 288,700,000            
Cash flows from financing activities:                                              
Draw down of revolving line of credit                 200,000,000 150,000,000 0       200,000,000 [5] 150,000,000 [5] 0 [5]            
Repayment of revolving line of credit                 (275,000,000) (75,000,000) 0       (275,000,000) [4],[5] (75,000,000) [4],[5] 0 [4],[5]           (75,000,000)
Proceeds from issuances of common shares                 0 0 900,000       0 0 900,000            
Repurchases and retirement of common shares                 (79,800,000) (669,100,000) (253,000,000)       (79,800,000) [3],[4] (669,100,000) [3],[4] (253,000,000) [3],[4]            
Dividends paid on common shares                 (6,200,000) (6,600,000) (8,000,000)       (6,200,000) (6,600,000) (8,000,000)            
Net cash used for financing activities                 (186,500,000) (648,200,000) (460,200,000)       (161,000,000) (600,700,000) (260,100,000)            
Net change in cash during the period                 114,100,000 (41,300,000) 223,400,000       (300,000) (200,000) 400,000            
Cash balance at beginning of year 326,700,000       212,600,000       326,700,000 212,600,000 251,900,000 103,600,000     200,000 500,000 700,000 300,000          
Cash balance at end of year 326,700,000       212,600,000       326,700,000 212,600,000 251,900,000 103,600,000     200,000 500,000 700,000 300,000          
Cash dividends received on warrants                         0           0     0  
Interest Paid                 42,600,000 44,600,000 59,000,000       3,700,000 2,000,000 12,400,000            
Noncash distribution received                         0                    
Common shares repurchased and retired during the period                   1,329,640                          
Noncash investments acquired                                       0 284.7    
Noncash payables acquired                           $ 417.5                  
[1] In November 2011, Lone Tree Insurance Group Ltd., a direct wholly-owned subsidiary of the Registrant, was liquidated into the Registrant. Significant non-cash balances that were transferred to the Registrant as part of the liquidation included fixed maturity investments of $1,146.9, short-term investments of $284.7 and a payable to subsidiary of $417.5.
[2] During 2013, the Company received a distribution of $28.0 from its direct wholly-owned subsidiary Lone Tree Holdings, Ltd. The distribution included $27.9 of fixed maturities and $.1 of cash. Purchases of investment securities excludes the non-cash distribution of $27.9.
[3] During 2012, the Company sold the majority of its fixed maturity investments and used the proceeds to (a) contribute $663.0 to its subsidiaries, the majority of which was used to fund HG Global and (b) repurchase 1,329,640 of its common shares for $669.1.
[4] During 2013, the Company used cash proceeds received from the issuance of debt to repurchase $79.8 of its common shares and repay $75.0 of its revolving line of credit.
[5] The WTM Bank Facility presented in Note 6 - “Debt” is a direct obligation of the Registrant.