Insider Trading March 23, 2026

Orange County Bancorp CEO Makes Mixed Insider Moves; Bank Announces Dividend and Executive Promotion

CEO Michael J. Gilfeather buys a small stake while selling shares to cover taxes; bank reports dividend and a senior promotion amid strategic activity at an affiliate trust

By Caleb Monroe OBT
Orange County Bancorp CEO Makes Mixed Insider Moves; Bank Announces Dividend and Executive Promotion
OBT

Orange County Bancorp President and CEO Michael J. Gilfeather reported both a purchase and a sale of company stock on March 19, 2026, according to a Form 4 filing. Gilfeather bought 200 shares for $6,249 and simultaneously sold 6,189 shares to satisfy tax obligations. The company also disclosed restricted stock unit grants and updates to outstanding holdings, while announcing a cash dividend and a senior promotion at its subsidiary. Separately, Osprey Bitcoin Trust has taken procedural steps to convert its shares into an exchange-traded product.

Key Points

  • CEO Michael J. Gilfeather bought 200 shares at $31.2499 and sold 6,189 shares at $31.15 on March 19, 2026 - the sale was to cover tax obligations. (Sector impact: regional banking / financials)
  • Gilfeather received 16,853 RSUs vesting one-third per year beginning March 19, 2027, and 9,438 RSUs vesting March 19, 2029, and now directly owns 129,449 shares plus indirect and phantom holdings. (Sector impact: corporate governance / compensation practices)
  • Orange County Bancorp declared a $0.18 per-share cash dividend payable March 16, 2026 to shareholders of record as of March 4, 2026; subsidiary promotion and Osprey Bitcoin Trust ETP conversion steps were also disclosed. (Sector impact: banking dividends and cryptocurrency ETP markets)

Insider transactions recorded

Orange County Bancorp (EXCHANGE:OBT) disclosed a set of insider transactions for President and CEO Michael J. Gilfeather in a Form 4 filed with the Securities and Exchange Commission. The filing shows Gilfeather purchased 200 shares of common stock at a price of $31.2499 per share, for a total cost of $6,249. On the same date, he disposed of 6,189 shares at $31.15 per share, generating proceeds of $192,787. The filing indicates the sale was made to cover tax obligations.

Vesting awards and ownership stakes

Also recorded in the filing were awards of restricted stock units. Gilfeather received 16,853 restricted stock units that vest at a rate of one-third per year beginning March 19, 2027, and an additional 9,438 restricted stock units that vest on March 19, 2029. After accounting for these transactions and previously held instruments, Gilfeather directly holds 129,449 shares of Orange County Bancorp, a total that includes restricted stock units vesting at various dates. He additionally holds 16,400 shares indirectly through an IRA and 26,460 shares of phantom stock that are payable upon separation of service as a director.

Market context

The company’s shares have climbed roughly 26% over the past six months. At the time of the report the stock was trading at $31.97 and the company carried a market capitalization of $427 million. Orange County Bancorp is trading at a P/E ratio of 9.6 and yields 2.25% in dividends.


Corporate actions and personnel update

In separate corporate disclosures, Orange County Bancorp, Inc. declared a cash dividend of $0.18 per share of common stock. The dividend will be paid on March 16, 2026, to shareholders of record as of March 4, 2026.

Orange Bank & Trust Company, a subsidiary of Orange County Bancorp, announced the promotion of Joseph A. Ruhl to Senior Executive Vice President. Ruhl has been employed by the bank since 2015 and is credited in the announcement with contributing to commercial expansion and business development efforts in the Westchester and Northern Hudson Valley markets.


Related trust activity

Separately noted in the filings, Osprey Bitcoin Trust has undertaken procedural steps to list its shares on the Nasdaq Stock Market as an exchange-traded product (ETP). To support this conversion and listing, Osprey Funds, LLC, and CSC Delaware Trust Company executed a revised Declaration of Trust and Trust Agreement.

What the filings show and what remains unchanged

The Form 4 provides the specific transaction prices, share counts, vesting schedules and ownership totals. It records the March 19, 2026 transaction date for the CEO’s purchase, sale and the restricted stock unit grants. The dividend declaration includes the payment date and the record date. The promotion at the subsidiary and the trust documentation for Osprey Bitcoin Trust are also reflected in corporate disclosures.

Risks

  • Insider sales to cover tax obligations could temporarily increase share supply and interact with short-term price movements - this affects the regional banking equity market.
  • The CEO’s restricted stock units vest over multi-year schedules, creating future dilution or concentration risks depending on how the grants are settled and exercised - relevant to shareholders assessing corporate compensation and dilution.
  • Market volatility reflected in a 26% six-month share price move underscores price risk for investors; the company’s dividend and valuation metrics do not eliminate short-term trading fluctuations - impacting investor returns in the financial sector.

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