[Form 4] Hagerty, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Hagerty, Inc. insider Diana Chafey, who serves as Chief Legal Officer, reported two transactions in early October 2025. On 10/01/2025 she disposed of 1,076 shares of Class A common stock at $11.95 per share; the filing explains these were shares withheld for taxes when restricted stock units vested from an award dated 10/01/2023. On 10/02/2025 she acquired 993 shares under Hagerty's Employee Stock Purchase Plan for the April 1–September 30, 2025 offering period, at a per‑share price equal to 95% of the closing price on 10/01/2025 ($11.35 shown). The Form 4 was signed via power of attorney on 10/03/2025.

Positive

• Participation in the ESPP with 993 shares purchased at a 5% discount demonstrates ongoing employee alignment with the company
• RSU vesting occurred (grant date 10/01/2023), indicating equity compensation is being delivered per plan

Negative

• Disposition of 1,076 shares at $11.95 was reported, which reduces the reporting person's direct holding
• Net change in shares is a modest decrease (55,941 to 56,934 shows reported holdings movement across days)

Insights

Corporate Governance Expert

Insider reported a tax-withholding sale and ESPP purchase in consecutive days.

The Form 4 discloses a tax withholding sale of 1,076 shares at $11.95 tied to RSU vesting, which is a common administrative step following equity vesting and does not itself indicate discretionary liquidation beyond tax obligations.

The subsequent ESPP purchase of 993 shares at 95% of the closing price shows continued participation in the company's employee purchase program; both actions are clearly documented and consistent with standard executive equity activity.

Compensation/Equity Plan Expert

Transactions reflect routine equity-plan mechanics: RSU vesting withholding and ESPP buy-in.

The filing states the RSU award had a grant date of 10/01/2023 and that shares were withheld for taxes, while ESPP shares were acquired for the offering period ending 9/30/2025. These entries document plan executions rather than new compensation terms or grants disclosed in this Form 4.

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

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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^*

Chafey Diana

(Last) (First) (Middle)

121 DRIVERS EDGE

(Street)

TRAVERSE CITY MI 49684

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Hagerty, Inc. [ HGTY ]

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

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Legal Officer

3. Date of Earliest Transaction (Month/Day/Year)
10/01/2025

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
Class A Common Stock	10/01/2025		F		1,076(1)	D	$11.95	55,941	D
Class A Common Stock	10/02/2025		A		993(2)	A	$11.35(3)	56,934	D

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

Explanation of Responses:

1. Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to Reporting Person's RSU award agreement with a grant date of October 1, 2023.

2. Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2025 through September 30, 2025.

3. In accordance with the ESPP, the per share price paid for these shares was an amount equal to 95% of the closing price of the Issuer's stock on October 1, 2025.

Remarks:

Exhibit 24 - Power of Attorney

	/s/ Tracey Derenzy, Power of Attorney	10/03/2025
	** 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 Hagerty insider Diana Chafey report on Form 4 (HGTY)?

She reported a sale of 1,076 Class A shares at $11.95 on 10/01/2025 and an ESPP purchase of 993 shares on 10/02/2025.

Why were 1,076 shares sold according to the Form 4?

The filing states those shares were withheld for taxes upon the vesting of RSUs from an award dated 10/01/2023.

At what price were the ESPP shares purchased?

Per the Form 4, ESPP shares were bought at 95% of the closing price on 10/01/2025, shown as $11.35 per share.

What is Diana Chafey's role at Hagerty?

The Form 4 identifies her as a Director and the company's Chief Legal Officer.

When was the Form 4 signed?

The filing shows a Power of Attorney signature by Tracey Derenzy on 10/03/2025.