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Employee Compensation Plans - Additional Information (Narrative) (Details)
12 Months Ended
Jan. 31, 2019
shares
Jan. 11, 2019
shares
Dec. 31, 2018
USD ($)
employee_compensation_plan
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Dec. 31, 2017
USD ($)
Dec. 31, 2016
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     $ 18,500 $ 18,000 $ 18,000
Employer contribution to Defined Contribution Plan     1,800,000 1,500,000 1,300,000
Deferred bonus amounts     $ 9,400,000 8,200,000 7,700,000
Vesting period of deferred bonus     5 years    
Deferred compensation plans cost     $ 6,100,000 17,100,000 11,800,000
Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Number of shares of Class A Stock available | shares     811,937    
Restricted Stock | Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Aggregate intrinsic value of ESP awards outstanding     $ 32,900,000    
Compensation expense relating to the share-based awards     6,000,000 5,600,000 5,200,000
Unrecognized compensation cost related to unvested share-based compensation     $ 11,200,000    
Cost is expected to be recognized over a weighted average period     1 year 9 months 24 days    
Granted, Number of shares | shares     333,959    
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period | shares     39,465    
Restricted Stock | Subsequent Event [Member] | Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Granted, Number of shares | shares 359,208        
Employee Stock Option          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Compensation expense relating to the share-based awards     $ 26,500 25,700 19,900
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 3,578        
Stock Appreciation Rights (SARs) [Member]          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Compensation expense relating to the share-based awards     $ 700,000 $ 6,900,000 $ 1,000,000
Cost is expected to be recognized over a weighted average period     2 years 1 month    
Aggregate intrinsic value of OARs outstanding and expected to vest     $ 9,200,000    
Liability related to the OARs     6,900,000    
Total unrecognized compensation cost     $ 6,500,000    
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   560,156      
Minimum [Member] | Restricted Stock | 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        
Maximum [Member] | Restricted Stock | 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        
Third Anniversary | Restricted Stock | Subsequent Event [Member] | Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Granted, Number of shares | shares 153,818        
Fifth Anniversary [Domain] | Restricted Stock | Subsequent Event [Member] | Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period | shares 205,390        
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | 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    
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Minimum [Member] | Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Vesting period under share based payment     3 years    
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | 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 2014 Incentive Plan (OIP) [Member] | Second Anniversary | Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Vesting percentage under share based payment     25.00%    
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Third Anniversary | Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Vesting percentage under share based payment     25.00%    
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Fourth Anniversary | Class A Stock          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Vesting percentage under share based payment     25.00%    
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | 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%    
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    
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     $ 46,500,000    
CIBC Deferred Compensation Plan          
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]          
Company's deferred compensation liability     $ 15,600,000