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Employee Compensation Plans - Additional Information (Narrative) (Details) |  |  |  |  | 12 Months Ended
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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 |  |

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