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Long-Term Debt (Details) - USD ($)
3 Months Ended 9 Months Ended
Dec. 31, 2019
Sep. 30, 2020
Jun. 30, 2020
Mar. 31, 2020
Sep. 30, 2020
Debt Instrument [Line Items]          
Repayments for FHLBC borrowings   $ 0     $ 2,000,000,000.00
FHLBC stock $ 43,393,000 5,000,000     5,000,000
Accrued interest payable 6,000,000 1,000,000     1,000,000
Notional amount 13,589,356,000 2,575,858,000     2,575,858,000
Accrued interest payable 60,655,000 34,225,000     34,225,000
Line of Credit | Non-Recourse Business Purpose Loan Financing Facility Two          
Debt Instrument [Line Items]          
Amount outstanding   158,000,000     158,000,000
Unamortized debt issuance costs   1,000,000     1,000,000
Debt instrument face amount   $ 157,000,000     157,000,000
Line of Credit | Non-Recourse Business Purpose Loan Financing Facility Two | LIBOR          
Debt Instrument [Line Items]          
Basis spread on variable rate   3.85%      
Reference rate floor   0.50%      
Line of Credit | Non-Recourse Business Purpose Loan Financing Facility One          
Debt Instrument [Line Items]          
Amount outstanding   $ 302,000,000     302,000,000
Unamortized debt issuance costs   4,000,000     4,000,000
Debt instrument face amount   298,000,000     298,000,000
Maximum borrowing limit     $ 530,000,000    
Line of Credit | Non-Recourse Business Purpose Loan Financing Facility One | Secured Debt          
Debt Instrument [Line Items]          
Maximum borrowing limit     355,000,000    
Line of Credit | Non-Recourse Business Purpose Loan Financing Facility One | Revolving Credit Facility          
Debt Instrument [Line Items]          
Maximum borrowing limit     $ 175,000,000    
Line of Credit | Non-Recourse Business Purpose Loan Financing Facility One | LIBOR          
Debt Instrument [Line Items]          
Basis spread on variable rate     7.50%    
Reference rate floor     1.50%    
Line of Credit | Recourse Business Purpose Loan Financing Facility Through September 2023          
Debt Instrument [Line Items]          
Amount outstanding   0     0
Maximum borrowing limit   $ 250,000,000     250,000,000
Line of Credit | Recourse Business Purpose Loan Financing Facility Through September 2023 | LIBOR          
Debt Instrument [Line Items]          
Basis spread on variable rate   3.00%      
Line of Credit | Recourse Business Purpose Loan Financing Facility          
Debt Instrument [Line Items]          
Amount outstanding   $ 150,000,000     150,000,000
Unamortized debt issuance costs   1,000,000     1,000,000
Debt instrument face amount   150,000,000     150,000,000
Maximum borrowing limit     $ 350,000,000    
Line of Credit | Recourse Business Purpose Loan Financing Facility | LIBOR          
Debt Instrument [Line Items]          
Reference rate floor     1.00%    
Line of Credit | Recourse Business Purpose Loan Financing Facility | LIBOR | Minimum          
Debt Instrument [Line Items]          
Basis spread on variable rate     3.50%    
Line of Credit | Recourse Business Purpose Loan Financing Facility | LIBOR | Maximum          
Debt Instrument [Line Items]          
Basis spread on variable rate     4.00%    
Line of Credit | Recourse Revolving Debt Facility          
Debt Instrument [Line Items]          
Amount outstanding   0     0
Maximum borrowing limit       $ 50,000,000  
Collateral amounts   33,000,000     33,000,000
Line of Credit | Recourse Revolving Debt Facility | LIBOR          
Debt Instrument [Line Items]          
Basis spread on variable rate       2.75%  
Bridge Loan | Non-Recourse Business Purpose Loan Financing Facility Two          
Debt Instrument [Line Items]          
Pledged assets real estate pledged as collateral, at fair value   216,000,000     216,000,000
Bridge Loan | Non-Recourse Business Purpose Loan Financing Facility One          
Debt Instrument [Line Items]          
Pledged assets real estate pledged as collateral, at fair value   369,000,000     369,000,000
Bridge Loan | Recourse Business Purpose Loan Financing Facility          
Debt Instrument [Line Items]          
Pledged assets real estate pledged as collateral, at fair value   18,000,000     18,000,000
Loans Payable | Non-Recourse Business Purpose Loan Financing Facility One          
Debt Instrument [Line Items]          
Pledged assets real estate pledged as collateral, at fair value   25,000,000     25,000,000
Loans Payable | Recourse Business Purpose Loan Financing Facility          
Debt Instrument [Line Items]          
Pledged assets real estate pledged as collateral, at fair value   $ 194,000,000     $ 194,000,000
Convertible Debt | Exchangeable Senior Notes Due 2025          
Debt Instrument [Line Items]          
Debt Instrument interest rate   5.75%     5.75%
Unamortized debt issuance costs   $ 4,000,000     $ 4,000,000
Convertible notes   172,000,000     172,000,000
Amount of debt repurchased   29,000,000     29,000,000
Gain (loss) on extinguishment of debt   6,000,000      
Accrued interest payable   $ 5,000,000     $ 5,000,000
Convertible Debt | Senior Notes Due 2024          
Debt Instrument [Line Items]          
Debt Instrument interest rate   5.625%     5.625%
Unamortized debt issuance costs   $ 2,000,000     $ 2,000,000
Convertible notes   150,000,000     150,000,000
Amount of debt repurchased   50,000,000     50,000,000
Gain (loss) on extinguishment of debt   9,000,000      
Accrued interest payable   2,000,000     2,000,000
Unamortized debt discount   $ 1,000,000     $ 1,000,000
Convertible Debt | Senior Notes Due 2023          
Debt Instrument [Line Items]          
Debt Instrument interest rate   4.75%     4.75%
Unamortized debt issuance costs   $ 3,000,000     $ 3,000,000
Convertible notes   199,000,000     199,000,000
Amount of debt repurchased   46,000,000     46,000,000
Gain (loss) on extinguishment of debt   10,000,000      
Accrued interest payable   1,000,000     1,000,000
Trust Preferred Securities          
Debt Instrument [Line Items]          
Debt instrument face amount   100,000,000     100,000,000
Subordinated Notes          
Debt Instrument [Line Items]          
Debt instrument face amount   40,000,000     40,000,000
Trust Preferred Securities and Subordinated Notes          
Debt Instrument [Line Items]          
Accrued interest payable 1,000,000 1,000,000     1,000,000
FHLB Chicago | FHLB Member Subsidiary          
Debt Instrument [Line Items]          
Federal home loan bank advances outstanding $ 2,000,000,000.00 $ 1,000,000     $ 1,000,000
Weighted average interest rate 1.88% 0.35%     0.35%
Weighted average maturity (in years) 6 years        
FHLB Chicago | Redwood | Held-for-sale residential loans | Restricted cash          
Debt Instrument [Line Items]          
Loans pledged as collateral under borrowing agreement with FHLBC   $ 1,000,000     $ 1,000,000
Affiliated Entity | Recourse Subordinate Securities Financing Facilities | Non-Marginable Debt Repurchase Agreement One          
Debt Instrument [Line Items]          
Debt Instrument interest rate 4.21%        
Amount outstanding   180,000,000     180,000,000
Unamortized debt issuance costs   1,000,000     1,000,000
Debt instrument face amount   179,000,000     179,000,000
Affiliated Entity | Recourse Subordinate Securities Financing Facilities | Non-Marginable Debt Repurchase Agreement Two          
Debt Instrument [Line Items]          
Debt Instrument interest rate     4.21%    
Amount outstanding   103,000,000     103,000,000
Unamortized debt issuance costs   1,000,000     1,000,000
Debt instrument face amount   102,000,000     102,000,000
Affiliated Entity | Sequoia Choice | Recourse Subordinate Securities Financing Facilities | Non-Marginable Debt Repurchase Agreement One          
Debt Instrument [Line Items]          
Pledged assets real estate pledged as collateral, at fair value   232,000,000     232,000,000
Affiliated Entity | CAFL | Recourse Subordinate Securities Financing Facilities | Non-Marginable Debt Repurchase Agreement Two          
Debt Instrument [Line Items]          
Pledged assets real estate pledged as collateral, at fair value   $ 112,000,000     $ 112,000,000