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Income Taxes (Details) (USD $)
12 Months Ended
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Dec. 31, 2007
Net deferred tax assets and liabilities [Abstract]        
Total deferred tax assets $ 1,043,477,000 $ 997,784,000 $ 683,645,000  
Total deferred tax liabilities (42,158,000) (44,350,000)    
Net deferred tax asset before valuation allowance 1,001,319,000 953,434,000    
Valuation allowance (1,004,256,000) (965,987,000) (608,800,000)  
Net deferred tax liability (2,937,000) (12,553,000)    
Components of net deferred tax liability [Abstract]        
Benefit plans (26,111,000) 77,000    
Net operating loss 915,378,000 866,700,000    
Loss reserves 36,236,000 55,615,000    
Unrealized (appreciation) depreciation in investments 29,230,000 (14,448,000)    
Mortgage investments 13,450,000 14,602,000    
Deferred compensation 15,994,000 13,288,000    
Premium deficiency reserves 16,961,000 25,823,000    
Other, net 181,000 (8,223,000)    
Net deferred tax asset before valuation allowance 1,001,319,000 953,434,000    
Valuation allowance (1,004,256,000) (965,987,000) (608,800,000)  
Net deferred tax liability (2,937,000) (12,553,000)    
Tax provision (benefit) [Abstract]        
Benefit from income taxes (17,239,000) (330,740,000) (196,835,000)  
Change in valuation allowance 20,935,000 329,175,000 198,428,000  
Provision for (benefit from) income taxes (note 14) 3,696,000 (1,565,000) 1,593,000  
Increase (decrease) in deferred tax valuation allowance, included in other comprehensive income 17,300,000 28,100,000 0  
Net operating loss carryforwards, regular tax basis 2,616,000,000      
Net operating loss carryforwards for computing the alternative minimum tax 1,731,000,000      
Components of provisions for (benefit from) income taxes [Abstract]        
Current 916,000 (4,251,000) 598,000  
Deferred 7,000 90,000 (945,000)  
Other 2,773,000 2,596,000 1,940,000  
Provision for (benefit from) income taxes 3,696,000 (1,565,000) 1,593,000  
Federal income tax received 0 7,000,000 0  
Federal income tax paid 100,000      
Reconciliation of effective income tax rate [Abstract]        
Federal statutory income tax benefit rate (in hundredths) (35.00%) (35.00%) (35.00%)  
Valuation allowance (in hundredths) 45.40% 35.40% 41.00%  
Tax exempt municipal bond interest (in hundredths) (3.70%) (0.80%) (5.40%)  
Other, net (in hundredths) 1.30% 0.20% (0.30%)  
Effective income tax (benefit) rate (in hundredths) 8.00% (0.20%) 0.30%  
Information regarding income tax examinations [Abstract]        
Amount of IRS assessment for unpaid taxes and penalties related to REMIC issue 197,500,000      
Estimate of federal interest that may be due 154,500,000      
Estimate of additional state income taxes and interest that may be due 46,000,000      
Amount of payment made related to the IRS assessment on the REMIC issue       65,200,000
Unrecognized tax benefits [Roll Forward]        
Balance at beginning of year 104,550,000 110,080,000 109,282,000  
Additions based on tax positions related to the current year 0 0 0  
Additions for tax positions of prior years 816,000 511,000 798,000  
Reductions for tax positions of prior years 0 (4,041,000) 0  
Settlements 0 (2,000,000) 0  
Balance at end of year 105,366,000 104,550,000 110,080,000  
Unrecognized tax benefits [Abstract]        
Total amount of unrecognized tax benefits that would affect effective tax rate 92,800,000      
Unrecognized tax benefits, interest expense 800,000      
Unrecognized tax benefits, accrued interest $ 26,100,000 $ 25,300,000