OBT Orange County Bancorp, Inc. /DE/ Insider Trading

CEO Michael J Gilfeather buys 200 OBT shares at $31.25; stock now $31.97, down 8.7% in 30 days despite 11.9% 90-day gain.

Gilfeather, as President and CEO, purchased 200 shares at $31.25, modestly increasing holdings to 16,400 shares post-transaction. At the current price of $31.97, the stock is -8.7% over 30 days yet +11.9% over 90 days, placing the transaction near recent lows within the 52-week range of $21.34–$35.56. His same-ticker history shows a split record: two purchases on 2025-10-31 each achieved +12.9% in 30 days and +28.1% in 90 days, but three earlier buys at OBT in 2024 and 2023 were substantially underwater, with the 2024-11-01 purchases down -46.4% in 30 days and -53.3% in 90 days. His cross-ticker track record across all buys shows an average 90-day return of -21.1% with a 33.33% win rate, indicating this insider's buy timing has historically been challenged. The fundamental backdrop is modest: P/E of 8.53 on $10.0M net income and a $427.4M market cap, characteristics that alone do not signal distress or exceptional value.

OBT CEO Michael J Gilfeather buys 1,650 shares for $39,633 after stock decline from 52-week high

Michael J Gilfeather, President and CEO of Orange County Bancorp, executed 2 open-market purchases totaling 1,650 shares for $39,633.00 at $24.02 per share on 2025-10-31, increasing his holdings by 1,650 shares to 16,200 shares post-transaction. The stock is currently at $24.72, down 22.5% from its 52-week high of $31.90, and has declined 0.7% over the past 30 days. However, Gilfeather's prior buy transactions at OBT show a concerning pattern: his 4 previous purchases at this ticker achieved 0 of 4 well-timed 90-day outcomes, with average 90-day returns of -46.0% (-53.3%, -53.3%, -38.1%, -38.1%). His broader cross-ticker track record shows 4 prior buys with a 0.00% 90-day win rate and an average 90-day return of -45.7%. The timing and context of this purchase warrant scrutiny given the historical pattern of negative outcomes following his prior accumulations at this security.

Director Schiller Jon purchased 6,451 shares of OBT at $23.25, doubling stake to 12,446 shares as stock trades 24.9% below 52-week high

Director Jon Schiller purchased 6,451 shares at $23.25, increasing his holdings by 107.6% from 5,995 to 12,446 shares, representing a $149,985.75 commitment. The purchase occurred with OBT trading at a material discount: $23.97 current price is 24.9% below the 52-week high of $31.90, and the stock has declined 9.5% over the past 30 days. At a P/E of 9.99 and market cap of $272.9M, the company trades at a low valuation multiple despite generating $8.7M in annual net income. The director's substantial increase in ownership stake—doubling his position in absolute terms—occurs against recent downward price momentum and a depressed valuation relative to recent trading ranges.

OBT CEO Michael J Gilfeather bought 525 shares for $29,226.75 at $55.67; stock now $26.64, down 52.1% from trade price.

Gilfeather executed 2 separate purchases totaling 525 shares at $55.67 on 2024-11-01, bringing his holdings from 7,400 to 7,925 shares. The current stock price of $26.64 is now significantly below the blended average purchase price of $55.67, representing substantial paper losses on the transaction. Gilfeather's cross-ticker track record shows 2 prior buys with an average 90-day return of -38.1% and a 0% win rate, while his prior trades at OBT (2 buys in September 2023) also exhibited poor 90-day performance of -38.1%. The company trades at a notably low P/E of 4.35 with market cap of $150,880,195.44 and net income of $8,213,000.00, but the insider's historical pattern of ill-timed purchases provides no confidence signal in this accumulation.