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Basis of Presentation and Significant Accounting Policies (Details) - USD ($)
$ in Thousands
1 Months Ended 3 Months Ended 9 Months Ended
Aug. 31, 2019
Nov. 30, 2018
Jun. 30, 2019
Aug. 31, 2019
Sep. 30, 2018
Aug. 31, 2019
Sep. 30, 2018
Loans and Leases Receivable Disclosure [Line Items]              
Revenues       $ 1,223,156 $ 1,458,977 $ 3,928,539 $ 3,863,914
Receivables from brokers, dealers and clearing organizations $ 2,931,000 $ 3,223,700   2,931,000   2,931,000  
Receivables from customers of securities operations 1,686,200 2,017,100   1,686,200   1,686,200  
Payables to brokers, dealers and clearing organizations 2,253,000 2,465,600   2,253,000   2,253,000  
Payables to customers of securities operations 3,599,600 3,176,700   3,599,600   3,599,600  
Cash paid during the year for:              
Interest           1,257,311 1,059,139
Income tax payments (refunds), net           25,825 28,204
Commissions and other fees              
Loans and Leases Receivable Disclosure [Line Items]              
Revenues       171,000 162,578 493,560 481,672
Other              
Loans and Leases Receivable Disclosure [Line Items]              
Revenues       169,248 289,387 351,544 419,888
Iowa Premium              
Loans and Leases Receivable Disclosure [Line Items]              
Membership Interest Purchase Agreement, Aggregate Ownership Interests To Purchase     100.00%        
Cash paid during the year for:              
Membership Interest Purchase Agreement, Proportionate Share     $ 49,000        
HomeFed              
Loans and Leases Receivable Disclosure [Line Items]              
Non-cash investing activities related to the issuance of common stock for acquisition           178,800  
Foursight Capital | Automobile Loan              
Loans and Leases Receivable Disclosure [Line Items]              
Loans and Leases Receivable, Gross $ 720,800 $ 648,700   $ 720,800   $ 720,800  
Credit Concentration Risk | Loans Receivable | Prime | Foursight Capital | Automobile Loan              
Loans and Leases Receivable Disclosure [Line Items]              
Concentration risk, percentage 15.00% 13.00%          
Credit Concentration Risk | Loans Receivable | Near-Prime | Foursight Capital | Automobile Loan              
Loans and Leases Receivable Disclosure [Line Items]              
Concentration risk, percentage 54.00% 57.00%          
Credit Concentration Risk | Loans Receivable | Subprime | Foursight Capital | Automobile Loan              
Loans and Leases Receivable Disclosure [Line Items]              
Concentration risk, percentage 31.00% 30.00%          
Reclassified presentation of certain other fees | Jefferies Group | Commissions and other fees              
Loans and Leases Receivable Disclosure [Line Items]              
Revenues         7,200   20,600
Reclassified presentation of certain other fees | Jefferies Group | Other              
Loans and Leases Receivable Disclosure [Line Items]              
Revenues         $ (7,200)   $ (20,600)