Esquire Financial Holdings, Inc. Form 4 Filings

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.

Esquire Financial Holdings, Inc. (ESQ) director Richard T. Powers reported a bona fide gift of 51,380 shares of common stock on August 25, 2026, transferring them to a Family Trust where they are now held indirectly. Following the transaction, he holds 6,853 shares directly, which include multiple tranches of restricted stock vesting between December 2024 and December 2027.

Esquire Financial Holdings, Inc. director Anthony Coelho exercised stock options for 20,000 shares of common stock on August 7, 2026 at an exercise price of $12.50 per share. In connection with this exercise, 1,902 shares of common stock were delivered or withheld for payment of exercise price or tax liability at $131.38 per share. The stock options exercised were fully vested. Following these transactions, Coelho reported indirect holdings of 12,910 shares of common stock held by a trust and 36,000 shares held by an IRA, with portions of his reported common stock position consisting of restricted stock that vests in full or in installments between December 2024 and December 2027.

Esquire Financial Holdings director Leonard Caronia exercised 2,232 stock options on August 4, 2026 at an exercise price of $19.57 per share, converting them into 2,232 shares of common stock held indirectly through a corporation. To cover the option exercise price or related tax obligations, 335 indirectly held shares were withheld at $130.31 per share. Caronia continues to hold multiple option grants on additional shares, many fully vested and others vesting annually beginning May 26, 2027, with exercise prices ranging from $22.41 to $111.14 and expirations from 2027 through 2036.

Esquire Financial Holdings, Inc. director Leonard Caronia reported merger-related equity acquisitions on August 1, 2026. In connection with the March 11, 2026 merger with Signature Bancorporation, 98864.0000 shares of common stock are indirectly held "By corporation," reflecting the 2.671-for-1 share conversion.

Multiple Signature stock options converted into options on Esquire common stock at adjusted exercise prices (for example, 2232.0000 shares at $19.5700 per share). Most converted options are fully vested, while the 950.0000-share series with a $111.1400 exercise price vests in five equal annual installments beginning May 26, 2027.

Esquire Financial Holdings, Inc. reporting person Michael G. O'Rourke, President of the Chicago Bank Division, reported multiple acquisitions on 2026-08-01 tied to the merger with Signature Bancorporation. Signature common stock and stock options converted into Esquire equity at a 2.671-for-1 ratio, resulting in 66726 common shares held directly and 18630 held indirectly via an IRA, plus several Esquire stock option awards with exercise prices from $19.5700 to $111.1400 per share. Most options are fully vested; one grant vests in five equal annual installments commencing on May 26, 2027.

Esquire Financial Holdings, Inc. director Robert Mitzman reported a sale of 3,000 shares of common stock on July 30, 2026 in a transaction coded as a sale in an open market or private transaction at $129.5973 per share. Following this sale, he directly holds 139,679 shares of common stock, which include multiple grants of restricted stock that vest between December 2024 and December 2027. He also holds 2,500 shares indirectly through an insurance trust I and 2,500 shares indirectly through an insurance trust II.

Esquire Financial Holdings director Richard T. Powers reported an open-market sale of 2,308 shares of Common Stock at $104.825 per share. After this transaction, he directly owns 58,233 shares. His holdings include multiple grants of restricted stock scheduled to vest in stages from December 2024 through December 2027.

Esquire Financial Holdings director Selig Zises reported net open-market sales of 30,000 shares of common stock. The transactions on March 18–19, 2026 were executed through indirect accounts, including a profit sharing plan and a trust, at prices around $105–$107 per share.

After these sales, reported indirect holdings include 6,501 shares in the profit sharing plan and 63,533 shares held by a trust, along with 15,716 shares held directly. Some reported holdings include restricted stock that will vest over future dates.

Esquire Financial Holdings, Inc. reported that SVP & Chief Financial Officer Michael Lacapria received an award of 1,164 shares of common stock on January 29, 2026 at a price of $0, indicating a restricted stock grant.

These shares of restricted stock vest in three equal annual installments commencing on January 29, 2029. Following this award, Lacapria beneficially owns 17,606 shares of common stock directly and 3,250 shares indirectly through an IRA. He also holds several stock option positions, with certain grants fully vested and others vesting in three equal annual installments commencing on December 15, 2024.

Esquire Financial Holdings EVP and COO Eric S. Bader reported an award of 3,492 shares of common stock on January 29, 2026. The shares are restricted stock that vest in three equal annual installments beginning January 29, 2029.

After this grant, Bader beneficially owns 139,116 shares of common stock directly, which include multiple restricted stock awards with different vesting schedules from 2024 through 2028. He also indirectly holds 2,000 shares through an IRA.

Esquire Financial Holdings, Inc. executive Ari P. Kornhaber, EVP and Head of Corporate Development, reported an equity award of common stock. On January 29, 2026, he received 5,122 shares of restricted stock at a price of $0 per share, reflecting a compensatory grant.

These restricted shares vest in three equal annual installments beginning on January 29, 2029119,792 shares of common stock and indirectly owns 1,947 shares through an IRA.

Esquire Financial Holdings Vice Chairman, President & CEO Andrew C. Sagliocca received an award of 8,148 shares of common stock on January 29, 2026. The shares were granted at $0 per share as restricted stock, a common form of equity compensation.

These restricted shares vest in three equal annual installments beginning on January 29, 2029298,798 shares directly, which include several prior restricted stock awards scheduled to vest in three annual installments starting on December 16, 2024; December 9, 2025; December 19, 2026; December 15, 2027; and January 30, 2028.

Esquire Financial Holdings, Inc. director Richard T. Powers reported routine equity transactions. On 01/05/2026, he exercised stock options for 1,500 shares of common stock at $24.9 per share, converting fully vested options granted on 12/10/2019 and expiring on 12/10/2028. On the same date, 359 shares of common stock were withheld at a price of $103.79 in a transaction coded "F," typically used for tax withholding. After these transactions, he directly beneficially owned 60,541 shares of common stock, which include multiple tranches of restricted stock scheduled to vest between December 2024 and December 2027.

Esquire Financial Holdings executive reports stock option exercises and share holdings. EVP and Head of Corporate Development Ari P. Kornhaber exercised stock options for 11,125 shares of common stock at $12.5 per share and separately for 7,500 shares at $12.5 per share on January 5, 2026. Following these transactions and a tax withholding transaction of 2,242 shares at $103.79 per share, he directly beneficially owned 114,670 shares of common stock. The filing also notes 1,947 shares of common stock held indirectly through an IRA and that his stock options are fully vested, with portions of his holdings including restricted stock that vests in equal annual installments between December 2024 and January 2028.

Esquire Financial Holdings EVP and COO Eric S. Bader reported several equity transactions on January 5, 2026. He exercised 14,125 stock options at an exercise price of $12.5 per share, receiving the same number of Esquire common shares. In a related transaction coded “F,” 1,701 common shares were withheld at a price of $103.79 per share, typically reflecting shares surrendered for tax obligations. After these transactions, Bader directly beneficially owned 135,624 shares of common stock and indirectly held 2,000 additional shares through an IRA. The filing notes that certain shares included in these totals are restricted stock that will vest in equal annual installments between 2024 and 2028, and confirms that the stock options exercised were fully vested.

Esquire Financial Holdings, Inc. Vice Chairman, President & CEO and director reported a disposition of 5,785 shares of common stock on 12/16/2025 at a price of $106.82 per share, coded as transaction type F. Following this transaction, the reporting person beneficially owns 270,452 shares of common stock.

These holdings include multiple grants of restricted stock that vest in three equal annual installments beginning on various dates from December 19, 2023 through January 30, 2028. The filer also holds stock options covering 29,250 shares of common stock with a $12.5 exercise price, which became exercisable on 09/01/2017 and expire on 09/01/2026 and are described as fully vested.

Esquire Financial Holdings, Inc. executive vice president and chief operating officer Eric S. Bader reported equity transactions in company stock. On 12/16/2025, 3,293 shares of common stock were disposed of in a transaction coded "F" at $106.82 per share, typically indicating shares withheld to cover taxes on vesting. After this, he beneficially owned 126,365 shares of common stock directly and 2,000 shares indirectly through an IRA. He also held fully vested stock options with an exercise price of $12.5 per share covering 14,125 shares of common stock, exercisable from 09/01/2017 until expiration on 09/01/2026. Several portions of his holdings include restricted stock scheduled to vest in three equal annual installments from 12/19/2023 through 01/30/2028.

Esquire Financial Holdings, Inc. reported an insider equity transaction by its EVP and Head of Corporate Development. The Form 4 shows a transaction in common stock2,229 shares$106.82100,418 shares1,947 shares

The filing also lists fully vested stock options$12.57,500 shares11,125 shares

Esquire Financial Holdings, Inc. reported an insider stock transaction by its SVP & Chief Financial Officer. On 12/16/2025, the officer disposed of 240 shares of common stock in a transaction coded “F” at a price of $106.82 per share, typically indicating shares withheld to cover taxes on equity vesting. Following this, the officer beneficially owns 16,622 shares of common stock directly and 3,250 shares indirectly through an IRA.

The filing also lists several stock option awards on common stock with exercise prices from $20.85 to $48.32 and expiration dates between 12/10/2028 and 12/15/2033. Some options are fully vested, while others vest in three equal annual installments beginning on dates in 2023 and 2024.

Esquire Financial Holdings, Inc. reported that one of its directors received a grant of 753 shares of restricted common stock on December 10, 2025, at a stated price of $0 per share. These restricted shares are scheduled to vest 100% on December 10, 2026.

After this grant, the reporting person beneficially owns 59,400 shares of common stock, including multiple prior restricted stock awards that vest in annual installments from December 19, 2023 through December 15, 2027. The director also holds 1,500 fully vested stock options with an exercise price of $24.9 per share, expiring on December 10, 2028.

Esquire Financial Holdings, Inc. disclosed that one of its directors acquired 753 shares of restricted common stock on December 10, 2025 at a price of $0 per share. These restricted shares vest 100% on December 10, 2026.

Following this award, the director beneficially owns 15,716 shares of common stock directly, along with indirect holdings of 25,500 shares as trustee for a trust, 12,600 shares through a limited partnership, 79,033 shares through another trust, and 21,001 shares through a profit sharing plan. The filing notes that these totals include multiple restricted stock grants scheduled to vest in three equal annual installments beginning on various dates between December 19, 2023 and December 15, 2027.

Esquire Financial Holdings, Inc. reported that one of its directors acquired 753 shares of common stock on December 10, 2025 at a price of $0, reflecting a grant of restricted stock.

These 753 restricted shares vest 100% on December 10, 2026. Following this award, the director beneficially owns 4,436 common shares directly and also holds 9,786 shares indirectly through an LLC II, 6,000 shares indirectly through the director's mother, and 127,531 shares indirectly through an LLC I, including restricted stock scheduled to vest in three equal annual installments beginning in 2026 and 2027.

Esquire Financial Holdings, Inc. reported an insider equity award by one of its directors. On 12/10/2025, the director acquired 1,836 shares of common stock as restricted stock at a price of $0. These restricted shares vest 100% on December 10, 2026.

Following this grant, the director beneficially owns 49,267 shares of common stock directly, 12,910 shares indirectly through a trust, and 36,000 shares indirectly through an IRA. The director also holds fully vested stock options covering 20,000 shares of common stock with an exercise price of $12.5 per share, expiring on 09/01/2026.

Esquire Financial Holdings, Inc. director reported acquiring 753 shares of restricted common stock on December 10, 2025 at a stated price of $0 per share. Following this grant, the director beneficially owns 72,401 shares of common stock directly.

The newly reported 753 restricted shares vest 100% on December 10, 2026. The total holding includes multiple prior restricted stock awards that vest in three equal annual installments beginning on December 19, 2023, December 9, 2025, December 19, 2026, December 3, 2027, and December 15, 2027. The director also holds fully vested stock options for 2,000 shares at $20.85 expiring December 16, 2030 and 1,750 shares at $31.04 expiring December 9, 2031.

Esquire Financial Holdings, Inc. disclosed that one of its directors received a grant of 753 shares of restricted common stock on December 10, 2025. The shares were awarded at $0 per share and are scheduled to vest 100% on December 10, 2026.

After this grant, the director beneficially owns 142,679 shares of common stock directly, which include multiple restricted stock awards that vest in three equal annual installments beginning on dates between December 19, 2023 and December 15, 2027. In addition, the director indirectly owns 2,500 shares through an insurance trust I and 2,500 shares through an insurance trust II.

Esquire Financial Holdings, Inc. disclosed that one of its directors acquired 753 shares of restricted common stock on December 10, 2025 at a stated price of $0 as a restricted stock award. After this transaction, the director beneficially owns 2,620 shares of common stock in direct ownership.

The 753 restricted shares are scheduled to vest 100% on December 10, 2026. The reported holdings also include additional restricted stock that will vest in three equal annual installments beginning on December 3, 2027.

Esquire Financial Holdings, Inc. reported an insider equity award involving one of its directors. On December 10, 2025, the director acquired 753 shares of common stock in a transaction reported with code "A" at a stated price of $0, indicating a grant rather than an open-market purchase.

These shares are described as restricted stock that will vest 100% on December 10, 2026. Following this transaction, the director beneficially owned 753 shares, held as direct ownership. The filing is made by a single reporting person in their capacity as a director.

Esquire Financial Holdings, Inc. reported that one of its directors acquired 753 shares of common stock as a restricted stock award on December 10, 2025, at a price of $0. These restricted shares vest 100% on December 10, 2026. Following this grant, the director beneficially owns 87,352 shares directly, plus 48,000 shares held indirectly as trustee for trusts and 12,000 shares held indirectly as custodian for children. The director also holds fully vested stock options covering 584 shares of common stock with an exercise price of $31.04, exercisable since December 9, 2022 and expiring on December 9, 2031.

Esquire Financial Holdings, Inc.'s senior vice president and chief financial officer reported a transaction in the company's common stock dated December 9, 2025. The filing shows a disposition of 300 shares of common stock, coded "F", at a price of $104.04 per share.

After this transaction, the officer beneficially owns 18,612 shares of common stock directly, which include restricted stock awards vesting in three equal annual installments commencing on December 19, 2023, December 16, 2024, December 9, 2025, December 19, 2026, December 15, 2027, and January 30, 2028, and 1,500 shares indirectly through an IRA. The officer also holds stock options covering 1,500 shares at an exercise price of $24.9 and four grants of 2,500 shares each at exercise prices of $20.85, $31.04, $42.3, and $48.32, with expiration dates on December 10, 2028, December 16, 2030, December 9, 2031, December 19, 2032, and December 15, 2033.

Esquire Financial Holdings, Inc. reported an insider transaction by its executive vice president and head of corporate development. On December 9, 2025, the officer disposed of 1,997 shares of common stock at $104.04 per share under transaction code "F," leaving 102,647 shares directly beneficially owned.

The officer also beneficially owns 1,947 shares of common stock indirectly through an IRA. The directly held common stock includes multiple restricted stock awards that vest in three equal annual installments beginning on various dates from December 19, 2023 through January 30, 2028, and the officer holds fully vested stock options for 7,500 shares and 11,125 shares at a $12.50 exercise price, expiring in 2026.

Esquire Financial Holdings, Inc. reported an insider transaction by a senior executive who serves as Vice Chairman, President & CEO and a director. On December 9, 2025, the executive disposed of 5,181 shares of common stock at $104.04 in a transaction coded "F," leaving 276,237 shares beneficially owned directly.

These holdings include multiple grants of restricted stock that vest in three equal annual installments beginning on dates from December 19, 2023 through January 30, 2028. The executive also holds fully vested stock options covering 29,250 shares with a $12.50 exercise price, expiring on September 1, 2026.