Orange County Bancorp Inc
NASDAQ: OBT · FINANCIAL SERVICES · BANKS - REGIONAL
Updated 2026-06-04
Orange County Bancorp Inc (OBT) Insider transactions
All transactions
| Date | Insider | Title | Type | Shares | Price | Value |
|---|---|---|---|---|---|---|
| 2026-03-19 | SOUSA, GREGORY | EVP and Deputy CLO | Buy | 5,056 | — | — |
| 2026-03-19 | SOUSA, GREGORY | EVP and Deputy CLO | Sale | 1,307 | $31.15 | $40713.05 |
| 2026-03-19 | RUHL, JOSEPH A | Reg Pres, Westchester County | Buy | 5,133 | — | — |
| 2026-03-19 | RUHL, JOSEPH A | Reg Pres, Westchester County | Sale | 1,377 | $31.15 | $42893.55 |
| 2026-03-19 | ROONEY, STEPHEN | SVP, Chief Credit Officer | Buy | 2,812 | — | — |
| 2026-03-19 | ROONEY, STEPHEN | SVP, Chief Credit Officer | Sale | 841 | $31.15 | $26197.15 |
| 2026-03-19 | LISTNER, MICHAEL | SVP and Chief Risk Officer | Buy | 2,827 | — | — |
| 2026-03-19 | LISTNER, MICHAEL | SVP and Chief Risk Officer | Sale | 832 | $31.15 | $25916.80 |
| 2026-03-19 | LESLER, MICHAEL | EVP, Chief Financial Officer | Buy | 5,059 | — | — |
| 2026-03-19 | LESLER, MICHAEL | EVP, Chief Financial Officer | Sale | 1,177 | $31.15 | $36663.55 |
| 2026-03-19 | JONES, ELIZABETH A | SVP, Chief Operating Officer | Buy | 3,792 | — | — |
| 2026-03-19 | JONES, ELIZABETH A | SVP, Chief Operating Officer | Sale | 656 | $31.15 | $20434.40 |
| 2026-03-19 | GILFEATHER, MICHAEL J | Director, President and CEO | Buy | 16,853 | — | — |
| 2026-03-19 | GILFEATHER, MICHAEL J | Director, President and CEO | Buy | 9,438 | — | — |
| 2026-03-19 | GILFEATHER, MICHAEL J | Director, President and CEO | Sale | 6,189 | $31.15 | $192787.35 |
| 2026-03-19 | GILFEATHER, MICHAEL J | Director, President and CEO | Buy | 200 | $31.25 | $6249.98 |
| 2026-03-19 | DINEEN, DAVID P | SVP, Dir. Wealth Services | Buy | 4,333 | — | — |
| 2026-03-19 | DINEEN, DAVID P | SVP, Dir. Wealth Services | Sale | 790 | $31.15 | $24608.50 |
| 2026-03-10 | SOUSA, GREGORY | EVP and Deputy CLO | Sale | 410 | $31.47 | $12902.70 |
| 2026-03-10 | RUHL, JOSEPH A | Reg Pres, Westchester County | Sale | 459 | $31.47 | $14444.73 |
| 2026-03-10 | ROONEY, STEPHEN | SVP, Chief Credit Officer | Sale | 133 | $31.47 | $4185.51 |
| 2026-03-10 | LISTNER, MICHAEL | SVP and Chief Risk Officer | Sale | 326 | $31.47 | $10259.22 |
| 2026-03-10 | LESLER, MICHAEL | EVP, Chief Financial Officer | Sale | 271 | $31.47 | $8528.37 |
| 2026-03-10 | JONES, ELIZABETH A | SVP, Chief Operating Officer | Sale | 220 | $31.47 | $6923.40 |
| 2026-03-10 | GILFEATHER, MICHAEL J | Director, President and CEO | Sale | 1,682 | $31.47 | $52932.54 |
| 2026-03-10 | DINEEN, DAVID P | SVP, Dir. Wealth Services | Sale | 277 | $31.47 | $8717.19 |
| 2026-03-10 | COULTER, MICHAEL J | EVP and CLO | Sale | 499 | $31.47 | $15703.53 |
| 2026-02-20 | SCHILLER, JON | Director | Sale | 995 | — | — |
| 2026-02-20 | ROWLEY, RICHARD B | Director | Sale | 995 | — | — |
| 2026-02-20 | ROUIS, JONATHAN F | Director | Sale | 995 | — | — |
| 2026-02-20 | MORRISON, WILLIAM D | Director | Sale | 995 | — | — |
| 2026-02-20 | KENNEDY, MARIANNA R | Director | Sale | 995 | — | — |
| 2026-02-20 | KEANE, KEVIN J | Director | Sale | 995 | — | — |
| 2026-02-20 | HOLCOMBE, GREGORY F | Director | Sale | 995 | — | — |
| 2026-02-19 | TIRADO, OLGA LUZ | Director | Buy | 866 | — | — |
| 2026-02-19 | SCHILLER, JON | Director | Buy | 866 | — | — |
| 2026-02-19 | ROWLEY, RICHARD B | Director | Buy | 866 | — | — |
| 2026-02-19 | ROUIS, JONATHAN F | Director | Buy | 866 | — | — |
| 2026-02-19 | MORRISON, WILLIAM D | Director | Buy | 866 | — | — |
| 2026-02-19 | KENNEDY, MARIANNA R | Director | Buy | 866 | — | — |
| 2026-02-19 | KEANE, KEVIN J | Director | Buy | 866 | — | — |
| 2026-02-19 | HOLCOMBE, GREGORY F | Director | Buy | 866 | — | — |
| 2026-02-19 | GILFEATHER, MICHAEL J | Director, President and CEO | Buy | 4,241 | — | — |
| 2026-02-06 | HOLCOMBE, GREGORY F | Director | Buy | 34,720 | — | — |
| 2026-01-02 | TIRADO, OLGA LUZ | Director | Buy | 176 | $28.35 | $4989.60 |
| 2026-01-02 | SCHILLER, JON | Director | Buy | 708 | $28.35 | $20071.80 |
| 2026-01-02 | ROWLEY, RICHARD B | Director | Buy | 799 | $28.35 | $22651.65 |
| 2026-01-02 | ROUIS, JONATHAN F | Director | Buy | 159 | $28.35 | $4507.65 |
| 2026-01-02 | KENNEDY, MARIANNA R | Director | Buy | 200 | $28.35 | $5670.00 |
| 2026-01-02 | KEANE, KEVIN J | Director | Buy | 708 | $28.35 | $20071.80 |
| 2026-01-02 | HOLCOMBE, GREGORY F | Director | Buy | 799 | $28.35 | $22651.65 |
| 2025-12-16 | TIRADO, OLGA LUZ | Director | Buy | 1 | $28.95 | $28.95 |
| 2025-12-16 | SOUSA, GREGORY | EVP and Deputy CLO | Buy | 23 | $28.95 | $665.85 |
| 2025-12-16 | SCHILLER, JON | Director | Buy | 19 | $28.95 | $550.05 |
| 2025-12-16 | ROWLEY, RICHARD B | Director | Buy | 141 | $28.95 | $4081.95 |
| 2025-12-16 | ROUIS, JONATHAN F | Director | Buy | 36 | $28.95 | $1042.20 |
| 2025-12-16 | MORRISON, WILLIAM D | Director | Buy | 7 | $28.95 | $202.65 |
| 2025-12-16 | LESLER, MICHAEL | EVP, Chief Financial Officer | Sale | 240 | $28.95 | $6948.00 |
| 2025-12-16 | KENNEDY, MARIANNA R | Director | Buy | 53 | $28.95 | $1534.35 |
| 2025-12-16 | KEANE, KEVIN J | Director | Buy | 97 | $28.95 | $2808.15 |
| 2025-12-16 | HOLCOMBE, GREGORY F | Director | Buy | 137 | $28.95 | $3966.15 |
| 2025-12-16 | GILFEATHER, MICHAEL J | Director, President and CEO | Buy | 136 | $28.95 | $3937.20 |
| 2025-12-11 | DINEEN, DAVID P | SVP, Dir. Wealth Services | Sale | 808 | $28.76 | $23238.08 |
| 2025-12-11 | DINEEN, DAVID P | SVP, Dir. Wealth Services | Sale | 192 | $29.00 | $5568.00 |
| 2025-12-05 | HOLCOMBE, GREGORY F | Director | Buy | 34,720 | — | — |
| 2025-11-10 | ROONEY, STEPHEN | SVP, Chief Credit Officer | Sale | 721 | $26.48 | $19092.08 |
| 2025-10-31 | GILFEATHER, MICHAEL J | Director, President and CEO | Buy | 1,300 | $24.02 | $31226.00 |
| 2025-10-31 | GILFEATHER, MICHAEL J | Director, President and CEO | Buy | 350 | $24.02 | $8407.00 |
| 2025-07-01 | TIRADO, OLGA LUZ | Director | Buy | 47 | $26.49 | $1245.03 |
| 2025-07-01 | SCHILLER, JON | Director | Buy | 729 | $26.49 | $19311.21 |
| 2025-07-01 | ROWLEY, RICHARD B | Director | Buy | 826 | $26.49 | $21880.74 |
| 2025-07-01 | ROUIS, JONATHAN F | Director | Buy | 170 | $26.49 | $4503.30 |
| 2025-07-01 | KEANE, KEVIN J | Director | Buy | 729 | $26.49 | $19311.21 |
| 2025-07-01 | HOLCOMBE, GREGORY F | Director | Buy | 826 | $26.49 | $21880.74 |
| 2025-06-16 | TIRADO, OLGA LUZ | Director | Buy | 1 | $23.14 | $23.14 |
| 2025-06-16 | SOUSA, GREGORY | EVP and Deputy CLO | Buy | 20 | $23.14 | $462.80 |
| 2025-06-16 | SCHILLER, JON | Director | Buy | 9 | $23.14 | $208.26 |
| 2025-06-16 | ROWLEY, RICHARD B | Director | Buy | 115 | $23.14 | $2661.10 |
| 2025-06-16 | ROUIS, JONATHAN F | Director | Buy | 31 | $23.14 | $717.34 |
| 2025-06-16 | MORRISON, WILLIAM D | Director | Buy | 6 | $23.14 | $138.84 |
| 2025-06-16 | LESLER, MICHAEL | EVP, Chief Financial Officer | Buy | 5 | $23.14 | $115.70 |
| 2025-06-16 | KENNEDY, MARIANNA R | Director | Buy | 48 | $23.14 | $1110.72 |
| 2025-06-16 | KEANE, KEVIN J | Director | Buy | 78 | $23.14 | $1804.92 |
| 2025-06-16 | HOLCOMBE, GREGORY F | Director | Buy | 113 | $23.14 | $2614.82 |
| 2025-06-16 | GILFEATHER, MICHAEL J | Director, President and CEO | Buy | 122 | $23.14 | $2823.08 |
| 2025-06-04 | SCHILLER, JON | Director | Buy | 6,451 | $23.25 | $149985.75 |
| 2025-05-28 | DINEEN, DAVID P | SVP, Dir. Wealth Services | Sale | 240 | $25.85 | $6204.00 |
| 2025-05-16 | RUHL, JOSEPH A | Reg Pres, Westchester County | Sale | 1,752 | $26.67 | $46725.84 |
| 2025-05-05 | COULTER, MICHAEL J | EVP and CLO | Sale | 2,497 | $26.17 | $65346.49 |
| 2025-05-02 | SOUSA, GREGORY | EVP and Deputy CLO | Sale | 1,813 | $24.60 | $44599.80 |
| 2025-05-02 | SOUSA, GREGORY | EVP and Deputy CLO | Sale | 300 | $24.61 | $7383.00 |
| 2025-05-02 | SOUSA, GREGORY | EVP and Deputy CLO | Sale | 177 | $24.65 | $4363.05 |
| 2025-05-02 | SOUSA, GREGORY | EVP and Deputy CLO | Sale | 100 | $24.62 | $2462.00 |
| 2025-05-02 | SOUSA, GREGORY | EVP and Deputy CLO | Sale | 50 | $25.00 | $1250.00 |
| 2025-04-30 | ROWLEY, RICHARD B | Director | Buy | 274 | $23.72 | $6499.28 |
| 2025-03-21 | SOUSA, GREGORY | EVP and Deputy CLO | Sale | 625 | $24.15 | $15093.75 |
| 2025-03-21 | RUHL, JOSEPH A | Reg Pres, Westchester County | Sale | 664 | $24.15 | $16035.60 |
| 2025-03-21 | ROWLEY, RICHARD B | Director | Buy | 1,124 | — | — |
| 2025-03-21 | ROWLEY, RICHARD B | Director | Sale | 1,102 | — | — |
| 2025-03-21 | ROUIS, JONATHAN F | Director | Buy | 1,124 | — | — |
Frequently asked questions
Are OBT insiders buying or selling?
Over the transactions on record, OBT insiders have been net buyers, with about $809121.23 in stock sold across 39 sales, against 39 open-market purchases.
Does insider selling at OBT mean the stock will fall?
Not by itself. Most executive selling is pre-scheduled through 10b5-1 plans filed months in advance, and insiders sell for diversification, taxes, and liquidity far more often than out of any view on the price. Insider buying is the stronger signal, especially when several insiders buy around the same time, because there is usually only one reason to put personal cash into the stock.
Which OBT insiders are selling the most?
Recent selling is concentrated in a few names. GILFEATHER, MICHAEL J accounts for the largest share on record, with about $245719.89 sold. Selling by one or two individuals matters less than broad selling across the whole leadership team, which is the pattern worth watching.