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Employee Compensation Plans - Additional Information (Narrative) (Details) |  |  | 12 Months Ended
--- | --- | --- | ---
Jan. 29, 2020 shares | Jan. 10, 2020 shares | Dec. 31, 2019 USD ($) employee_compensation_plan shares | Dec. 31, 2018 USD ($) | Dec. 31, 2017 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 |  |  | $ 19,000 | $ 18,500 | $ 18,000
Employer contribution to Defined Contribution Plan |  |  | 2,400,000 | 1,800,000 | 1,500,000
Deferred bonus amounts |  |  | $ 9,300,000 | 9,400,000 | 8,200,000
Vesting period of deferred bonus |  |  | 5 years |  |
Deferred compensation plans cost |  |  | $ 19,400,000 | 6,100,000 | 17,100,000
Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Number of shares of Class A Stock available | shares |  |  | 450,840 |  |
Restricted Stock | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Aggregate intrinsic value of ESP awards outstanding |  |  | $ 42,200,000 |  |
Compensation expense relating to the share-based awards |  |  | 8,100,000 | 6,000,000 | 5,600,000
Unrecognized compensation cost related to unvested share-based compensation |  |  | $ 12,200,000 |  |
Cost is expected to be recognized over a weighted average period |  |  | 1 year 4 months 24 days |  |
Granted, Number of shares | shares |  |  | 379,728 |  |
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period | shares |  |  | 112,465 |  |
Restricted Stock | Subsequent Event [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Granted, Number of shares | shares | 409,125 |  |  |  |
Employee Stock Option |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Compensation expense relating to the share-based awards |  |  | $ 26,200 | 26,500 | 25,700
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 | 3,142 |  |  |  |
Stock Appreciation Rights (SARs) [Member] |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Compensation expense relating to the share-based awards |  |  | $ 3,700,000 | $ 650,000 | $ 6,900,000
Cost is expected to be recognized over a weighted average period |  |  | 2 years 11 months |  |
Aggregate intrinsic value of OARs outstanding and expected to vest |  |  | $ 11,000,000 |  |
Liability related to the OARs |  |  | 9,400,000 |  |
Total unrecognized compensation cost |  |  | $ 6,300,000 |  |
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 |  | 547,560 |  |  |
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 | 211,575 |  |  |  |
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 | 197,550 |  |  |  |
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] |  |  |  |  |
Company's deferred compensation liability |  |  | $ 51,200,000 |  |
CIBC Deferred Compensation Plan |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Company's deferred compensation liability |  |  | $ 18,800,000 |  |

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