Old Second Bancorp Inc (OSBC)

Old Second Bancorp Inc. has seen significant insider selling over the past 90 days, with a net value of approximately $1.16 million in sales. Key executives, including Vice Chairman Gary S. Collins and EVP Donald Pilmer, were primary sellers. These transactions occurred amid a 23.7% stock price increase, with the stock trading near its 52-week high.
Ticker: OSBC Exchange: NSM


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Insider trades have triggered activity signals for Old Second Bancorp Inc. Upgrade to see score, net flow, insiders and the full signal context.

Top insiders
Trades
Sale 22 May 2026
Value US$149,290.26 | Price 357.27 | Shares 50,057 (-19.5%)
Abbreviations B: Buy, S: Sell, PP: Planned purchase, PlS: Planned sale, PrS: Proposed sale, O: Option / Other
Notification date Transaction date B/S Transaction type Insider and/or position Nb. shares
Price
Value
Number of shares Price Value Details
2026-05-26 2026-05-22 S Sale

VICE CHAIRMAN

Executive Director
50,057 -19.5%
357.27
US$149,290
50,057 -19.5% 357.27 US$149,290
2026-05-21 2026-05-21 S Sale

VICE CHAIRMAN

Executive Director
10,607 -14.6%
219.57
US$2,211,131
10,607 -14.6% 219.57 US$2,211,131
2026-05-12 2026-05-11 B Purchase Non-Executive Director
80,573 +19.0%
115.54
US$1,882,215
80,573 +19.0% 115.54 US$1,882,215
2026-05-11 2026-05-11 S Sale

EVP

Officer
25,000 -34.2%
20.75
US$518,795
25,000 -34.2% 20.75 US$518,795
2026-05-11 2026-05-08 S Sale

VICE CHAIRMAN

Executive Director
5,000 -6.4%
21.23
US$106,125
5,000 -6.4% 21.23 US$106,125
2026-05-11 2026-05-08 S Sale

VICE CHAIRMAN

Executive Director
10,000 -24.9%
21.24
US$212,400
10,000 -24.9% 21.24 US$212,400
2026-03-23 2026-03-20 S Sale

VICE CHAIRMAN

Executive Director
22,154 -35.6%
19.38
US$429,435
22,154 -35.6% 19.38 US$429,435
2026-02-19 2026-02-18 S Sale

President, Powersports Lending

Executive Director
35,000 -11.3%
20.94
US$732,900
35,000 -11.3% 20.94 US$732,900
2026-02-18 2026-02-13 S Sale

President, Powersports Lending

Executive Director
91 -0.0%
20.70
US$1,884
91 -0.0% 20.70 US$1,884
2026-02-05 2026-02-05 S Sale

EVP

Officer
2,000 -7.4%
20.98
US$41,950
2,000 -7.4% 20.98 US$41,950
2026-01-16 2026-01-15 S Sale Non-Executive Director
1,865 -1.3%
20.96
US$39,090
1,865 -1.3% 20.96 US$39,090
2026-01-16 2026-01-15 S Sale Non-Executive Director
2,897 -1.9%
20.94
US$60,666
2,897 -1.9% 20.94 US$60,666
2025-12-09 2025-12-09 S Sale Non-Executive Director
12,500 -7.7%
20.00
US$250,000
12,500 -7.7% 20.00 US$250,000
2025-11-26 2025-11-26 S Sale Non-Executive Director
13,150 -7.5%
19.01
US$249,991
13,150 -7.5% 19.01 US$249,991
2025-11-07 2025-10-31 S Sale

President, Powersports Lending

Executive Director
31,159 -100.0%
17.89
US$557,313
31,159 -100.0% 17.89 US$557,313
2025-11-07 2025-10-30 S Sale

President, Powersports Lending

Executive Director
26,406 -45.9%
18.27
US$482,329
26,406 -45.9% 18.27 US$482,329
2025-08-05 2025-08-04 B Purchase Non-Executive Director
25 +0.1%
16.61
US$415
25 +0.1% 16.61 US$415
2025-02-11 2025-02-10 B Purchase Non-Executive Director
22 +0.2%
19.02
US$418
22 +0.2% 19.02 US$418
2024-12-26 2024-12-23 B Purchase Non-Executive Director
5,625 +43.1%
17.79
US$100,068
5,625 +43.1% 17.79 US$100,068
2024-11-12 2024-11-06 S Sale Non-Executive Director
13,888 -7.3%
18.27
US$253,696
13,888 -7.3% 18.27 US$253,696
2024-11-05 2024-11-04 B Purchase Non-Executive Director
26 +0.2%
16.15
US$420
26 +0.2% 16.15 US$420
2024-08-06 2024-08-05 B Purchase Non-Executive Director
23 +0.2%
14.86
US$342
23 +0.2% 14.86 US$342
2024-07-23 2024-07-22 S Sale Non-Executive Director
30,585 -13.9%
16.22
US$496,018
30,585 -13.9% 16.22 US$496,018
2024-05-09 2024-05-08 S Sale

VICE CHAIRMAN

Executive Director
21,002 -31.1%
14.23
US$298,808
21,002 -31.1% 14.23 US$298,808
2024-05-07 2024-05-06 B Purchase Non-Executive Director
24 +0.2%
14.44
US$347
24 +0.2% 14.44 US$347
2024-05-07 2024-05-06 B Purchase Non-Executive Director
24 +0.2%
14.44
US$347
24 +0.2% 14.44 US$347
2024-04-24 2024-04-23 S Sale

VICE CHAIRMAN

Executive Director
22,267 -24.8%
14.57
US$324,430
22,267 -24.8% 14.57 US$324,430
2024-04-24 2024-04-23 S Sale

VICE CHAIRMAN

Executive Director
15,000 -19.5%
14.55
US$218,250
15,000 -19.5% 14.55 US$218,250
2024-04-24 2024-04-22 S Sale

VICE CHAIRMAN

Executive Director
3,000 -3.2%
14.48
US$43,440
3,000 -3.2% 14.48 US$43,440
2024-02-07 2024-02-06 B Purchase Non-Executive Director
26 +0.3%
13.46
US$350
26 +0.3% 13.46 US$350
2022-12-19 2022-12-16 B Purchase

VICE CHAIRMAN

Executive Director
900 +0.7%
16.04
US$14,432
900 +0.7% 16.04 US$14,432
2022-11-03 2022-11-02 B Purchase Non-Executive Director
10,000 +13.2%
16.44
US$164,400
10,000 +13.2% 16.44 US$164,400
2022-09-19 2022-09-16 B Purchase

VICE CHAIRMAN

Executive Director
1,000 +0.8%
13.35
US$13,350
1,000 +0.8% 13.35 US$13,350
2023-03-28 2022-06-09 B Purchase Non-Executive Director
3,000 +42.1%
15.13
US$45,390
3,000 +42.1% 15.13 US$45,390
2022-05-19 2022-05-18 B Purchase Non-Executive Director
4,000 +5.6%
14.18
US$56,720
4,000 +5.6% 14.18 US$56,720
2022-04-11 2022-04-11 S Sale Non-Executive Director
4,557 -6.9%
14.20
US$64,696
4,557 -6.9% 14.20 US$64,696
2022-03-14 2022-03-14 S Sale Non-Executive Director
4,557 -6.4%
14.46
US$65,894
4,557 -6.4% 14.46 US$65,894
2022-02-14 2022-02-14 S Sale Non-Executive Director
4,557 -6.0%
14.31
US$65,211
4,557 -6.0% 14.31 US$65,211
2022-02-09 2022-02-08 B Purchase Non-Executive Director
23 +0.2%
14.42
US$332
23 +0.2% 14.42 US$332
2022-01-10 2022-01-10 S Sale Non-Executive Director
4,557 -5.8%
13.44
US$61,246
4,557 -5.8% 13.44 US$61,246
2021-11-08 2021-11-08 S Sale Non-Executive Director
4,557 -5.3%
14.01
US$63,844
4,557 -5.3% 14.01 US$63,844
2021-08-17 2021-08-13 B Purchase

Vice Chairman

Executive Director
4,144 +352.4%
12.06
US$49,992
4,144 +352.4% 12.06 US$49,992
2021-08-17 2021-08-13 B Purchase

Vice Chairman

Executive Director
1,000 +1.4%
11.77
US$11,765
1,000 +1.4% 11.77 US$11,765
2021-08-17 2021-08-13 B Purchase

Vice Chairman

Executive Director
1,000 +0.9%
11.97
US$11,968
1,000 +0.9% 11.97 US$11,968
2021-08-12 2021-08-12 B Purchase

CEO

Executive Director
1,422 +31.3%
11.54
US$16,407
1,422 +31.3% 11.54 US$16,407
2021-08-12 2021-08-12 B Purchase

CEO

Executive Director
7,367 +32.6%
11.54
US$85,000
7,367 +32.6% 11.54 US$85,000
2021-08-11 2021-08-09 B Purchase

Vice Chairman

Executive Director
1,000 +0.9%
11.40
US$11,400
1,000 +0.9% 11.40 US$11,400
2021-03-24 2021-03-23 B Purchase Non-Executive Director
4,000 +100.0%
13.40
US$53,580
4,000 +100.0% 13.40 US$53,580
2021-03-09 2021-03-08 S Sale Non-Executive Director
14,500 -6.2%
13.76
US$199,520
14,500 -6.2% 13.76 US$199,520
2021-03-08 2021-03-08 S Sale

EVP

Officer
1,500 -5.0%
13.63
US$20,445
1,500 -5.0% 13.63 US$20,445
2021-02-25 2021-02-25 S Sale

Chairman

Executive Director
6,313 -7.1%
11.95
US$75,440
6,313 -7.1% 11.95 US$75,440
2021-02-25 2021-02-25 S Sale

Chairman

Executive Director
100 -0.1%
11.96
US$1,196
100 -0.1% 11.96 US$1,196
2021-02-25 2021-02-25 S Sale

Chairman

Executive Director
87 -0.1%
11.97
US$1,041
87 -0.1% 11.97 US$1,041
2021-02-19 2021-02-19 B Purchase Non-Executive Director
125 +1.4%
11.45
US$1,431
125 +1.4% 11.45 US$1,431
2021-02-02 2021-02-01 B Purchase Non-Executive Director
654 +21.4%
10.09
US$6,599
654 +21.4% 10.09 US$6,599
2021-02-02 2021-02-01 B Purchase Non-Executive Director
43 +1.2%
10.10
US$434
43 +1.2% 10.10 US$434
2021-02-02 2021-02-01 B Purchase Non-Executive Director
613 +16.4%
10.13
US$6,210
613 +16.4% 10.13 US$6,210
2021-02-02 2021-02-01 B Purchase Non-Executive Director
256 +5.9%
10.14
US$2,596
256 +5.9% 10.14 US$2,596
2021-02-02 2021-02-01 B Purchase Non-Executive Director
734 +15.9%
10.15
US$7,450
734 +15.9% 10.15 US$7,450
2020-12-22 2020-12-21 S Sale Non-Executive Director
2,500 -11.0%
9.74
US$24,350
2,500 -11.0% 9.74 US$24,350
2020-12-14 2020-12-14 B Purchase Non-Executive Director
2,000 +100.0%
10.12
US$20,235
2,000 +100.0% 10.12 US$20,235
2020-12-14 2020-12-10 S Sale Non-Executive Director
350 -1.5%
10.35
US$3,622
350 -1.5% 10.35 US$3,622
2020-11-10 2020-11-10 B Purchase Non-Executive Director
100 +inf%
9.96
US$996
100 +inf% 9.96 US$996
2020-11-10 2020-11-10 B Purchase Non-Executive Director
1,800 +1800.0%
9.97
US$17,944
1,800 +1800.0% 9.97 US$17,944
2020-11-10 2020-11-10 B Purchase Non-Executive Director
100 +5.3%
9.96
US$996
100 +5.3% 9.96 US$996
2020-07-02 2020-06-30 B Purchase

CEO

Executive Director
83
0.00
US$0
83 0.00 US$0
2020-07-02 2020-06-30 B Purchase

CEO

Executive Director
7
0.00
US$0
7 0.00 US$0
2020-05-01 2020-05-01 B Purchase

CEO

Executive Director
9,966 +82.3%
8.31
US$82,817
9,966 +82.3% 8.31 US$82,817
2020-05-01 2020-05-01 B Purchase

CEO

Executive Director
2,067 +84.5%
8.13
US$16,805
2,067 +84.5% 8.13 US$16,805
2020-04-28 2020-04-27 B Purchase Non-Executive Director
1,099 +9.9%
6.97
US$7,660
1,099 +9.9% 6.97 US$7,660
2020-04-28 2020-04-27 B Purchase Non-Executive Director
601 +4.9%
6.95
US$4,177
601 +4.9% 6.95 US$4,177
2020-04-28 2020-04-27 B Purchase Non-Executive Director
300 +2.4%
6.96
US$2,088
300 +2.4% 6.96 US$2,088
2019-08-21 2019-08-21 B Purchase COLLINS GARY S

Vice Chairman

Executive Director
426 +92.2%
12.48
US$5,317
426 +92.2% 12.48 US$5,317
2019-07-30 2019-07-30 S Sale

Chairman

Executive Director
1,898 -2.1%
13.24
US$25,130
1,898 -2.1% 13.24 US$25,130
2019-07-30 2019-07-29 S Sale

Chairman

Executive Director
1,502 -1.6%
13.29
US$19,962
1,502 -1.6% 13.29 US$19,962
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