Orange County Bancorp (OBT) CEO Reports Large Share Disposition and Deferred Equity

Rhea-AI Filing Summary

Michael J. Gilfeather, President and CEO and a director of Orange County Bancorp, Inc. (OBT), reported multiple changes in his beneficial ownership on a Form 4 filed for transactions dated 09/16/2025. The filing shows a disposition of 105,488 shares of common stock and direct ownership of 15,850 shares held in an IRA after the reported transactions. The report also records acquisition of 109 units of phantom stock (each economically equivalent to one common share) and 21,919 shares underlying exercised or acquired awards priced at $25.95. Restricted stock units with various vesting schedules are included in the holdings, and the phantom stock becomes payable upon separation of service.

Positive

• Continued alignment with shareholders through retained deferred compensation (RSUs and phantom stock) that vest over future dates
• Disclosure completeness: the Form 4 lists vesting schedules, IRA holdings, and nature of phantom stock, meeting Section 16 transparency requirements

Negative

• Large disposition of 105,488 shares reported on 09/16/2025, which could increase share supply in the market
• No explanation provided in the filing for the reason or method of the disposal (e.g., open-market sale vs plan), limiting context for investors

Insights

Financial Analyst

TL;DR: CEO reported a large share disposition and retained meaningful direct and deferred interests, including phantom stock and RSUs with staggered vesting.

The disposal of 105,488 shares on 09/16/2025 is the most material item in the filing and may affect near-term float depending on market absorption, though the filing does not state whether the sale was open-market or part of a pre-arranged plan. The reporting person still holds 15,850 shares directly in an IRA and 21,919 shares attributable to phantom or option-like awards, plus multiple RSU tranches with scheduled vesting dates through 2026. Without total outstanding share count or context on company float, the filing’s market impact cannot be quantified from the document alone.

Corporate Governance Expert

TL;DR: Insider sold a substantial block while retaining deferred compensation tied to company equity; governance disclosures are standard for Section 16 reporting.

The Form 4 discloses both outright dispositions and retained deferred-equity interests (RSUs and phantom stock) with clear vesting schedules and a separation-based payout for phantom stock. The signature via power of attorney is properly executed. The filing provides required transparency about the timing and nature of insider transactions but does not include any explanations for the sale, which is common practice on Form 4s.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

Gilfeather Michael J

(Last) (First) (Middle)

212 DOLSON AVENUE

(Street)

MIDDLETOWN NY 10940

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Orange County Bancorp, Inc. /DE/ [ OBT ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President and CEO

3. Date of Earliest Transaction (Month/Day/Year)
09/16/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock								105,488(1)(2)(3)(4)	D
Common Stock								15,850	I	By IRA

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Phantom Stock	(5)	09/16/2025		A		$109		(5)	(5)	Common Stock	109	$25.95	21,919	D

Explanation of Responses:

1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 11, 2024.

2. Includes restricted stock units which vest on December 31, 2026.

3. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.

4. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 20, 2026.

5. Each share of phantom stock is the economic equivalent of one share of common stock and becomes payable upon the reporting person's separation of service as a director.

	/s/ Jennifer Staub, pursuant to power of attorney	09/17/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What did OBT CEO Michael J. Gilfeather report on the Form 4 dated 09/16/2025?

The Form 4 reports a disposition of 105,488 common shares, direct ownership of 15,850 shares in an IRA after the transactions, acquisition of 109 units of phantom stock, and 21,919 shares underlying awards priced at $25.95.

Does the filing show retained equity compensation for Michael J. Gilfeather (OBT)?

Yes. The filing lists multiple restricted stock units (RSUs) with staggered vesting schedules and phantom stock that becomes payable upon separation of service.

When did the reported transactions occur for OBT insider activity?

The transactions listed on the Form 4 occurred on 09/16/2025, and the Form 4 was signed on 09/17/2025 by power of attorney.

What is the economic nature of the phantom stock reported on the Form 4?

Each phantom stock unit is stated to be the economic equivalent of one common share and becomes payable upon the reporting person's separation of service.

Are vesting schedules disclosed in the Form 4 for the reported equity awards?

Yes. The filing discloses RSUs vesting 1/3 per year commencing March 11, 2024, RSUs vesting on December 31, 2026, and additional RSU tranches with vesting commencing March 21, 2025 and March 20, 2026.