Esquire Financial director exercises 5,953 options

Esquire Financial Holdings, Inc. (ESQ) reported that director and President of the Chicago Bank Division Michael G. O'Rourke exercised stock options on September 14, 2026 to acquire 5,953 shares of common stock at an exercise price of $19.57 per share.

Rhea-AI Filing Summary

Esquire Financial Holdings, Inc. (ESQ) reported that director and President of the Chicago Bank Division Michael G. O'Rourke exercised stock options on September 14, 2026 to acquire 5,953 shares of common stock at an exercise price of $19.57 per share. Following this transaction, he owned 72,679 common shares directly and 18,630 common shares indirectly through an IRA. The options exercised were fully vested, and he continues to hold additional stock option awards with exercise prices ranging from $22.41 to $111.14 per share and expiration dates extending through May 26, 2036. No Rule 10b5-1 trading plan is reported for these transactions.

Insider Trade Summary

5,953 shares exercised/converted

Exercise 13 txns

Insider O'ROURKE MICHAEL G

Role President of Chicago Bank Div

Type	Security	Shares	Price	Value
Exercise	Stock Options F1	5,953	$0.00	$0.00
Exercise	Common Stock	5,953	$19.57	$117K
holding	Stock Options F1	--	--	--
holding	Stock Options F1	--	--	--
holding	Stock Options F1	--	--	--
holding	Stock Options F1	--	--	--
holding	Stock Options F1	--	--	--
holding	Stock Options F1	--	--	--
holding	Stock Options F1	--	--	--
holding	Stock Options F1	--	--	--
holding	Stock Options F1	--	--	--
holding	Stock Options F2	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Stock Options — 24,830 contracts (Direct); Common Stock — 72,679 shares (Direct); Common Stock — 18,630 shares (Indirect, By IRA)

Footnotes (2)

1. F1. Stock options are fully vested.
2. F2. Stock options vest in five equal annual installments commencing on May 26, 2027.

Key Figures

Shares acquired via option exercise: 5,953 shares Exercise price per share: $19.57 per share Direct common shares after transaction: 72,679 shares +3 more

6 metrics

Shares acquired via option exercise 5,953 shares Common stock acquired on September 14, 2026 through option exercise

Exercise price per share $19.57 per share Stock options exercised into common stock on September 14, 2026

Direct common shares after transaction 72,679 shares Direct ownership of ESQ common stock following the September 14, 2026 exercise

Indirect common shares held by IRA 18,630 shares Indirect ownership of ESQ common stock through an IRA as of September 14, 2026

Remaining option exercise price example $22.41 per share One remaining stock option award exercisable for 4,807 underlying shares, expiring August 1, 2027

Highest remaining option exercise price $111.14 per share Stock option award with 1,861 underlying shares, expiring May 26, 2036

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did ESQ report for Michael G. O'Rourke?

Michael G. O'Rourke exercised stock options to acquire 5,953 shares of Esquire Financial Holdings, Inc. common stock on September 14, 2026 at an exercise price of $19.57 per share, increasing his directly held common shares.

How many ESQ shares does Michael G. O'Rourke hold after this Form 4 transaction?

After the reported transaction, Michael G. O'Rourke directly held 72,679 shares of Esquire Financial common stock and indirectly held 18,630 shares through an IRA, as of September 14, 2026.

What was the exercise price of the ESQ options exercised by Michael G. O'Rourke?

The stock options exercised by Michael G. O'Rourke on ESQ common stock had an exercise price of $19.57 per share. These options were fully vested at the time of exercise and were originally scheduled to expire on October 1, 2026.

Does the ESQ Form 4 indicate a Rule 10b5-1 trading plan for this transaction?

No. The filing indicates that the transactions reported for Michael G. O'Rourke were not made under a Rule 10b5-1 trading plan, so they are not described as pre-arranged under such a plan.

What ESQ stock options does Michael G. O'Rourke continue to hold after this Form 4?

Michael G. O'Rourke continues to hold multiple stock option awards on ESQ common stock with exercise prices ranging from $22.41 to $111.14 per share and expiration dates between August 1, 2027 and May 26, 2036.

What is Michael G. O'Rourke’s role at Esquire Financial Holdings, Inc. (ESQ)?

Michael G. O'Rourke is reported as both a director and an officer of Esquire Financial Holdings, Inc., serving as President of the Chicago Bank Division.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 09/15/2026 - 04:04 PM Accepted by SEC EDGAR 09/15/2026 - 04:03 PM Learn about SEC filing dates

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).

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^*

O'ROURKE MICHAEL G

(Last) (First) (Middle)

100 JERICHO QUADRANGLE

SUITE 100

(Street)

JERICHO NEW YORK 11753

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Esquire Financial Holdings, Inc. [ ESQ ]

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

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President of Chicago Bank Div

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
09/14/2026

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

X	Form 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)
			Code	V	Amount	(A) or (D)	Price
Common Stock	09/14/2026		M		5,953	A	$19.57	72,679	D
Common Stock								18,630	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
Stock Options	$19.57	09/14/2026		M			5,953(1)	10/01/2017	10/01/2026	Common Stock	5,953(1)	$0	0	D
Stock Options	$22.41							08/01/2018	08/01/2027	Common Stock	4,807(1)		4,807(1)	D
Stock Options	$29.66							07/01/2019	07/01/2028	Common Stock	4,137(1)		4,137(1)	D
Stock Options	$36.73							10/01/2020	10/01/2029	Common Stock	2,671(1)		2,671(1)	D
Stock Options	$35.39							10/01/2021	10/01/2030	Common Stock	1,976(1)		1,976(1)	D
Stock Options	$42.97							07/01/2022	07/01/2031	Common Stock	2,003(1)		2,003(1)	D
Stock Options	$52.23							07/01/2023	07/01/2032	Common Stock	1,816(1)		1,816(1)	D
Stock Options	$62.34							07/01/2024	07/01/2033	Common Stock	1,842(1)		1,842(1)	D
Stock Options	$70.77							07/01/2025	07/01/2034	Common Stock	1,856(1)		1,856(1)	D
Stock Options	$80.87							07/01/2026	07/01/2035	Common Stock	1,861(1)		1,861(1)	D
Stock Options	$111.14							05/26/2027	05/26/2036	Common Stock	1,861(2)		1,861(2)	D

Explanation of Responses:

1. Stock options are fully vested.

2. Stock options vest in five equal annual installments commencing on May 26, 2027.

	/s/ Eric S. Bader, pursuant to power of attorney	09/15/2026
	** 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.
* Form 4: SEC 1474 (03-26)