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[Form 4] Orange County Bancorp, Inc. /DE/ Insider Trading Activity

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Lesler Michael reported acquisition or exercise transactions in this Form 4 filing.

Orange County Bancorp, Inc. executive vice president and chief financial officer Michael Lesler reported updated equity holdings, including a new award of phantom stock tied to the company’s Performance-Based SERP. The phantom stock grant, recorded at $35.35 per unit with 13.0000 underlying common shares, brings his total phantom stock interests to 2,532 units.

Lesler also reported indirect holdings of 2,000 shares of common stock in an IRA and 1,623 shares in a 401(k), along with 16,216 shares held directly. Some of these positions include restricted stock units that vest in thirds beginning on March 21, 2025, March 20, 2026, and March 19, 2027. Phantom stock interests under the Performance-Based SERP may be settled in company shares upon distribution, based on his prior election.

Positive

  • None.

Negative

  • None.
Insider Lesler Michael
Role EVP, Chief Financial Officer
Type Security Shares Price Value
Grant/Award Phantom Stock 0 $35.35 --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
Holdings After Transaction: Phantom Stock — 2,532 shares (Direct, null); Common Stock — 16,216 shares (Direct, null); Common Stock — 1,623 shares (Indirect, By 401(k))
Footnotes (1)
  1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 20, 2026. Restricted stock units which vest at a rate of 1/3 per year commencing on March 19, 2027. Reflects transactions not required to be reported pursuant to Section 16 of the Securities Exchange Act of 1934, as amended. Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests under the Performance-Based SERP may be settled in shares of Company stock upon distribution to the reporting person, based on their prior election.
Phantom stock price $35.35 per unit Recorded grant value for phantom stock
Underlying common shares 13 shares Common stock underlying new phantom stock interests
Total phantom stock interests 2,532 units Phantom stock balance after the grant
Direct common stock 16,216 shares Direct holdings of Orange County Bancorp common stock
IRA common stock 2,000 shares Indirect holdings via IRA
401(k) common stock 1,623 shares Indirect holdings via 401(k) plan
Phantom stock financial
"Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests..."
A phantom stock is a form of compensation that gives employees or executives the benefits of stock ownership, such as the increase in stock value, without actually giving them real shares. It acts like a promise to pay the employee the equivalent value of company stock later, often as a bonus or incentive. This allows companies to motivate and reward staff without diluting ownership or transferring actual shares.
Performance-Based SERP financial
"Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests..."
restricted stock units financial
"Includes restricted stock units which vest at a rate of 1/3 per year..."
Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.
Section 16 of the Securities Exchange Act of 1934 regulatory
"Reflects transactions not required to be reported pursuant to Section 16 of the Securities Exchange Act of 1934..."
A provision of federal securities law that requires company insiders—directors, officers and large shareholders—to publicly report their stock holdings and trades and to surrender any “short-swing” profits from purchases and sales within a six-month window. It acts like a rule that forces leaders to announce their trades and prevents quick buy-sell windfalls, giving investors transparency into insider activity and reducing opportunities for unfair gain.
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SEC Form 4
FORM 4UNITED 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).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Lesler Michael

(Last)(First)(Middle)
212 DOLSON AVENUE

(Street)
MIDDLETOWN NEW YORK 10940

(City)(State)(Zip)

UNITED STATES

(Country)
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)
Director10% Owner
XOfficer (give title below)Other (specify below)
EVP, Chief Financial Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
06/15/2026
6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

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)
CodeVAmount(A) or (D)Price
Common Stock16,216(1)(2)(3)D
Common Stock1,623(4)IBy 401(k)
Common Stock2,000IBy 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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Phantom Stock(5)06/15/2026A$13 (5) (5)Common Stock13$35.352,532D
Explanation of Responses:
1. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 21, 2025.
2. Includes restricted stock units which vest at a rate of 1/3 per year commencing on March 20, 2026.
3. Restricted stock units which vest at a rate of 1/3 per year commencing on March 19, 2027.
4. Reflects transactions not required to be reported pursuant to Section 16 of the Securities Exchange Act of 1934, as amended.
5. Represents deemed investments in connection with the Performance-Based SERP. Phantom stock interests under the Performance-Based SERP may be settled in shares of Company stock upon distribution to the reporting person, based on their prior election.
/s/ Jennifer Staub, pursuant to power of attorney06/16/2026
** Signature of Reporting PersonDate
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.
* Form 4: SEC 1474 (03-26)