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Condensed Consolidating Financial Information - Condensed Consolidating Statement of Operations (Details) - USD ($)
$ in Thousands
 3 Months Ended 6 Months Ended
Jun. 30, 2016
Jun. 30, 2015
Jun. 30, 2016
Jun. 30, 2015
REVENUES        
Commissions $ 92,591 $ 103,556 [1] $ 196,424 $ 213,251 [1]
Advisory fees 66,104 72,243 [1] 132,130 143,209 [1]
Investment banking 18,881 29,020 [1] 31,264 56,325 [1]
Interest 12,007 11,313 [1] 25,049 22,016 [1]
Principal transactions, net 7,577 3,541 [1] 14,195 12,038 [1]
Other 14,914 8,286 [1] 27,968 18,295 [1]
Total revenue 212,074 227,959 [1] 427,030 465,134 [1]
EXPENSES        
Compensation and related expenses 141,721 153,805 [1] 290,216 314,629 [1]
Communications and technology 17,638 16,307 [1] 35,318 33,379 [1]
Occupancy and equipment costs 14,984 15,911 [1] 29,887 31,612 [1]
Clearing and exchange fees 6,199 6,231 [1] 13,120 12,633 [1]
Interest 4,972 4,105 [1] 9,839 7,875 [1]
Other 31,806 32,701 [1] 61,236 60,293 [1]
Total expenses 217,320 229,060 [1] 439,616 460,421 [1]
Income (loss) before income taxes (5,246) (1,101) [1] (12,586) 4,713 [1]
Income taxes (2,627) 400 [1] (6,439) 2,555 [1]
Net income (loss) from continuing operations (2,619) (1,501) [1] (6,147) 2,158 [1]
Income attributable to noncontrolling interest before income taxes 15,366 3,731 [1] 14,709 7,768 [1]
Tax effect of discontinued operation 6,036 1,585 [1] 5,760 3,160 [1]
Net income from discontinued operations 9,330 2,146 [1] 8,949 4,608 [1]
Equity in earnings of subsidiaries 0 0 0 0
Net income 6,711 645 [1] 2,802 6,766 [1]
Less net income attributable to noncontrolling interests 1,523 350 [1] 1,461 752 [1]
Net income attributable to Oppenheimer Holdings Inc. 5,188 295 [1] 1,341 6,014 [1]
Other comprehensive income (loss) (654) 1,317 219 750
Comprehensive income attributable to Oppenheimer Holdings Inc. 4,534 1,612 1,560 6,764
Eliminations [Member]        
REVENUES        
Commissions 0 0 0 0
Advisory fees (407) (411) (760) (865)
Investment banking 0 0 0 0
Interest (2,565) (2,565) (5,132) (5,129)
Principal transactions, net 0 (30) 0 (84)
Other (80) (76) (158) (151)
Total revenue (3,052) (3,082) (6,050) (6,229)
EXPENSES        
Compensation and related expenses 0 0 0 0
Communications and technology 0 0 0 0
Occupancy and equipment costs (80) (76) (158) (151)
Clearing and exchange fees 0 0 0 0
Interest (2,565) (2,565) (5,132) (5,129)
Other (407) (441) (760) (949)
Total expenses (3,052) (3,082) (6,050) (6,229)
Income (loss) before income taxes 0 0 0 0
Income taxes 0 0 0 0
Net income (loss) from continuing operations 0 0 0 0
Income attributable to noncontrolling interest before income taxes 0 0 0 0
Tax effect of discontinued operation 0 0 0 0
Net income from discontinued operations 0 0 0 0
Equity in earnings of subsidiaries (10,564) (3,551) (6,522) (18,095)
Net income (10,564) (3,551) (6,522) (18,095)
Less net income attributable to noncontrolling interests 0 0 0 0
Net income attributable to Oppenheimer Holdings Inc. (10,564) (3,551) (6,522) (18,095)
Other comprehensive income (loss) 0 0 0 0
Comprehensive income attributable to Oppenheimer Holdings Inc. (10,564) (3,551) (6,522) (18,095)
Parent Company [Member]        
REVENUES        
Commissions 0 0 0 0
Advisory fees 0 0 0 0
Investment banking 0 0 0 0
Interest 0 0 0 0
Principal transactions, net 0 0 0 0
Other 0 0 0 0
Total revenue 0 0 0 0
EXPENSES        
Compensation and related expenses 356 263 743 575
Communications and technology 34 42 62 67
Occupancy and equipment costs 0 0 0 0
Clearing and exchange fees 0 0 0 0
Interest 3,282 3,281 6,563 6,562
Other 523 258 1,196 546
Total expenses 4,195 3,844 8,564 7,750
Income (loss) before income taxes (4,195) (3,844) (8,564) (7,750)
Income taxes (3,272) (1,521) (4,986) (3,001)
Net income (loss) from continuing operations (923) (2,323) (3,578) (4,749)
Income attributable to noncontrolling interest before income taxes 0 0 0 0
Tax effect of discontinued operation 0 0 0 0
Net income from discontinued operations 0 0 0 0
Equity in earnings of subsidiaries 6,111 2,618 4,919 10,763
Net income 5,188 295 1,341 6,014
Less net income attributable to noncontrolling interests 0 0 0 0
Net income attributable to Oppenheimer Holdings Inc. 5,188 295 1,341 6,014
Other comprehensive income (loss) 0 0 0 0
Comprehensive income attributable to Oppenheimer Holdings Inc. 5,188 295 1,341 6,014
Guarantor Subsidiaries [Member]        
REVENUES        
Commissions 0 0 0 0
Advisory fees 0 0 0 0
Investment banking 0 0 0 0
Interest 2,556 2,557 5,113 5,123
Principal transactions, net 22 0 52 0
Other 81 96 159 191
Total revenue 2,659 2,653 5,324 5,314
EXPENSES        
Compensation and related expenses 0 0 0 0
Communications and technology 0 0 0 0
Occupancy and equipment costs 0 0 0 0
Clearing and exchange fees 0 0 0 0
Interest 0 0 0
Other 2 45 5 113
Total expenses 2 45 5 113
Income (loss) before income taxes 2,657 2,608 5,319 5,201
Income taxes 999 923 2,003 1,770
Net income (loss) from continuing operations 1,658 1,685 3,316 3,431
Income attributable to noncontrolling interest before income taxes 0 0 0 0
Tax effect of discontinued operation 0 0 0 0
Net income from discontinued operations 0 0 0 0
Equity in earnings of subsidiaries 4,453 933 1,603 7,332
Net income 6,111 2,618 4,919 10,763
Less net income attributable to noncontrolling interests 0 0 0 0
Net income attributable to Oppenheimer Holdings Inc. 6,111 2,618 4,919 10,763
Other comprehensive income (loss) 0 0 0 0
Comprehensive income attributable to Oppenheimer Holdings Inc. 6,111 2,618 4,919 10,763
Non-Guarantor Subsidiaries [Member]        
REVENUES        
Commissions 92,591 103,556 196,424 213,251
Advisory fees 66,511 72,654 132,890 144,074
Investment banking 18,881 29,020 31,264 56,325
Interest 12,016 11,321 25,068 22,022
Principal transactions, net 7,555 3,571 14,143 12,122
Other 14,913 8,266 27,967 18,255
Total revenue 212,467 228,388 427,756 466,049
EXPENSES        
Compensation and related expenses 141,365 153,542 289,473 314,054
Communications and technology 17,604 16,265 35,256 33,312
Occupancy and equipment costs 15,064 15,987 30,045 31,763
Clearing and exchange fees 6,199 6,231 13,120 12,633
Interest 4,255 3,389 8,408 6,442
Other 31,688 32,839 60,795 60,583
Total expenses 216,175 228,253 437,097 458,787
Income (loss) before income taxes (3,708) 135 (9,341) 7,262
Income taxes (354) 998 (3,456) 3,786
Net income (loss) from continuing operations (3,354) (863) (5,885) 3,476
Income attributable to noncontrolling interest before income taxes 15,366 3,731 14,709 7,768
Tax effect of discontinued operation 6,036 1,585 5,760 3,160
Net income from discontinued operations 9,330 2,146 8,949 4,608
Equity in earnings of subsidiaries 0 0 0 0
Net income 5,976 1,283 3,064 8,084
Less net income attributable to noncontrolling interests 1,523 350 1,461 752
Net income attributable to Oppenheimer Holdings Inc. 4,453 933 1,603 7,332
Other comprehensive income (loss) (654) 1,317 219 750
Comprehensive income attributable to Oppenheimer Holdings Inc. $ 3,799 $ 2,250 $ 1,822 $ 8,082
[1] Amounts have been recast to reflect discontinued operations. See Note 3 for details.