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Employee Compensation Plans - Additional Information (Narrative) (Details)
12 Months Ended
Mar. 01, 2018
shares
Jan. 31, 2018
shares
Jan. 30, 2018
shares
Jan. 05, 2018
shares
Dec. 31, 2017
USD ($)
employee_compensation_plan
shares
Dec. 31, 2016
USD ($)
Dec. 31, 2015
USD ($)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Number of Employee Compensation Plans Granted | employee_compensation_plan         2    
Maximum annual contribution under Defined Contribution Plan         $ 18,000 $ 18,000 $ 18,000,000,000
Employer contribution to Defined Contribution Plan         1,500,000 1,300,000 1,600,000
Deferred bonus amounts         $ 8,200,000 7,700,000 8,300,000
Vesting period of deferred bonus         5 years    
Deferred compensation plans cost         $ 17,100,000 11,800,000 8,600,000
Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Number of shares of Class A Stock available | shares         1,143,598    
Restricted Stock | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Aggregate intrinsic value of ESP awards outstanding         $ 28,600,000    
Compensation expense relating to the share-based awards         5,600,000 5,200,000 4,600,000
Unrecognized compensation cost related to unvested share-based compensation         $ 9,800,000    
Cost is expected to be recognized over a weighted average period         2 years 2 months 24 days    
Granted, Number of shares | shares         464,100    
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period | shares         548,062    
Employee Stock Option              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Compensation expense relating to the share-based awards         $ 25,700 19,900 69,900
Employee Stock Option | Subsequent Event [Member] | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment     4 years 6 months        
Number of Options, Granted | shares     4,050        
Stock Appreciation Rights (SARs) [Member]              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Compensation expense relating to the share-based awards         $ 6,900,000 $ 1,000,000 $ 1,800,000
Cost is expected to be recognized over a weighted average period         2 years 2 months    
Aggregate intrinsic value of OARs outstanding and expected to vest         $ 15,000,000    
Liability related to the OARs         7,100,000    
Total unrecognized compensation cost         $ 8,300,000    
Stock Appreciation Rights (SARs) [Member] | Subsequent Event [Member]              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment       5 years      
Number Of Stock Appreciation Rights Granted | shares       497,430      
Employee Share Plan | Minimum [Member] | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment         3 years    
Employee Share Plan | Maximum [Member] | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment         5 years    
Oppenheimer Holdings Inc. Stock Appreciation Right Plan | Stock Appreciation Rights [Member]              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment         5 years    
Equity Incentive Plan | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Term granted for options         5 years    
Share-based Compensation Arrangement by Share-based Payment Award, Expiration Period         6 months    
Equity Incentive Plan | Second Anniversary | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting percentage under share based payment         25.00%    
Equity Incentive Plan | Third Anniversary | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting percentage under share based payment         25.00%    
Equity Incentive Plan | Fourth Anniversary | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting percentage under share based payment         25.00%    
Equity Incentive Plan | Six Months Before Expiration | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting percentage under share based payment         25.00%    
Stock Incentive Plan 2014 | Subsequent Event [Member] | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Granted, Number of shares | shares     281,919        
Stock Incentive Plan 2014 | Subsequent Event [Member] | Class A Stock | Executive Officer [Member]              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment   5 years          
Granted, Number of shares | shares   9,100          
Stock Incentive Plan 2014 | Subsequent Event [Member] | Class A Stock | Non Employee Director              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting percentage under share based payment 25.00%            
Granted, Number of shares | shares 17,500            
Stock Incentive Plan 2014 | Minimum [Member] | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment         3 years    
Stock Incentive Plan 2014 | Maximum [Member] | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment         5 years    
Stock Incentive Plan 2014 | Third Anniversary | Subsequent Event [Member] | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment     3 years        
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period | shares     126,240        
Stock Incentive Plan 2014 | Fifth Anniversary [Domain] | Subsequent Event [Member] | Class A Stock              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Vesting period under share based payment     5 years        
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period | shares     155,679        
Executive Deferred Compensation Plan and Deferred Incentive Plan              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Liability Percentage offset by Company Owned Life Insurance         60.00%    
Company's deferred compensation liability         $ 52,300,000    
CIBC Deferred Compensation Plan              
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]              
Company's deferred compensation liability         $ 17,200,000