HGTY · Hagerty, Inc. · Insider Trading

Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2026 through September 30, 2026.

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, 2026.

Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2026 through September 30, 2026.

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, 2026.

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.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of restricted stock units ("RSUs") pursuant to the RSU Agreement between the Issuer and the Reporting Person dated as of October 1, 2025.

Represents a bona fide gift to a charitable organization.

Held by Aldel LLC. The Reporting Person is the manager of Aldel LLC and has voting and investment discretion with respect to the securities held of record by Aldel LLC. The Reporting Person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest therein.

Each share of Class V Common Stock is paired with one unit of limited liability company interest of The Hagerty Group, LLC (each, an "OpCo Unit" and, together with each corresponding share of Class V Common Stock, a "Paired Interest"). Each Paired Interest has no expiration date and is exchangeable, at the option of the holder, on a one-for-one basis for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, an equivalent value in cash, pursuant to the Exchange Agreement, dated as of December 2, 2021, and amended and restated as of March 23, 2022, among the Reporting Person, The Hagerty Group, LLC, Hagerty Holding Corp., and the Issuer (the "Amended and Restated Exchange Agreement"). Each share of Class V Common Stock has no incidents of economic ownership and has ten (10) votes per share until the earlier of (i) December 2, 2036, and (ii) transfer to a non-qualified transferee, after which it has one (1) vote per share.

In connection with an underwritten secondary offering of shares of Class A Common Stock by Hagerty Holding Corp. that closed on September 11, 2026, and pursuant to the terms of the Amended and Restated Exchange Agreement, the Reporting Person exchanged 7,836,411 Paired Interests for, at the election of the Issuer, an equal number of shares of Class A Common Stock.

1,387,500 shares of Class A Common Stock were issued to the Reporting Person in exchange for an equal number of Paired Interests that were surrendered by the Reporting Person pursuant to the Exchange Agreement.

In connection with an underwritten secondary offering of shares of Class A Common Stock by Hagerty Holding Corp. that closed on September 11, 2026, and pursuant to the terms of the Amended and Restated Exchange Agreement, the Reporting Person exchanged 7,836,411 Paired Interests for, at the election of the Issuer, an equal number of shares of Class A Common Stock.

Each share of Class V Common Stock is paired with one unit of limited liability company interest of The Hagerty Group, LLC (each, an "OpCo Unit" and, together with each corresponding share of Class V Common Stock, a "Paired Interest"). Each Paired Interest has no expiration date and is exchangeable, at the option of the holder, on a one-for-one basis for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, an equivalent value in cash, pursuant to the Exchange Agreement, dated as of December 2, 2021, and amended and restated as of March 23, 2022, among the Reporting Person, The Hagerty Group, LLC, Hagerty Holding Corp., and the Issuer (the "Amended and Restated Exchange Agreement"). Each share of Class V Common Stock has no incidents of economic ownership and has ten (10) votes per share until the earlier of (i) December 2, 2036, and (ii) transfer to a non-qualified transferee, after which it has one (1) vote per share.

Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

1,387,500 shares of Class A Common Stock were issued to the Reporting Person in exchange for an equal number of Paired Interests that were surrendered by the Reporting Person pursuant to the Exchange Agreement.

Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

9,250,000 shares of Class A Common Stock were issued to the Reporting Person in exchange for an equal number of Paired Interests (as defined below) that were surrendered by the Reporting Person pursuant to the Amended and Restated Exchange Agreement, dated as of December 2, 2021 and amended and restated as of March 23, 2022 (the "Exchange Agreement"), among the Issuer, The Hagerty Group, LLC ("OpCo"), the Reporting Person, Markel Corporation ("Markel") and each of the Reporting Person's and Markel's Qualified Transferees (as defined therein). Each "Paired Interest" consists of one share of Class V Common Stock of the Issuer and one unit of limited liability company interest of OpCo and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

9,250,000 shares of Class A Common Stock were issued to the Reporting Person in exchange for an equal number of Paired Interests (as defined below) that were surrendered by the Reporting Person pursuant to the Amended and Restated Exchange Agreement, dated as of December 2, 2021 and amended and restated as of March 23, 2022 (the "Exchange Agreement"), among the Issuer, The Hagerty Group, LLC ("OpCo"), the Reporting Person, Markel Corporation ("Markel") and each of the Reporting Person's and Markel's Qualified Transferees (as defined therein). Each "Paired Interest" consists of one share of Class V Common Stock of the Issuer and one unit of limited liability company interest of OpCo and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 5, 2026.

The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 5, 2026.

This transaction was executed in multiple trades at prices ranging from $12.00 to $12.23. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on July 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of restricted stock units ("RSUs") pursuant to the RSU Agreement between the Issuer and the Reporting Person dated as of July 1, 2024.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of restricted stock units ("RSUs") pursuant to the RSU Agreement between the Issuer and the Reporting Person dated as of July 1, 2023.

The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 5, 2026.

This transaction was executed in multiple trades at prices ranging from $12.00 to $12.03. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

This transaction was executed in multiple trades at prices ranging from $10.44 to $10.46. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

The sale occurred automatically pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on November 10, 2025, and does not represent a discretionary transaction. The reported sale represents a "sell to cover" transaction and equals the number of shares required to be sold by the Reporting Person to satisfy tax withholding obligations in connection with the vesting of the Reporting Person's restricted stock units.

This transaction was executed in multiple trades at prices ranging from $10.91 to $11.10. The price reported above reflects the weighted average purchase price. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares and prices at which the transaction was effected.

Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of October 1, 2025 through March 31, 2026.

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 April 1, 2026.

Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of October 1, 2025 through March 31, 2026.

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 April 1, 2026.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements

Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to various RSU award agreements.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents shares of Class A Common Stock of Hagerty, Inc. ("Class A Common Stock") underlying restricted stock units ("RSUs") acquired by the Reporting Person under the Hagerty, Inc. (the "Issuer") 2021 Equity Incentive Plan (the "Plan"). The RSUs vest in equal amounts on each annual-anniversary of the grant date ending on April 1, 2029, subject to the Reporting Person's continued service with the Issuer, with exceptions for death, disability, or retirement terminations, or a change of control of the Issuer.

Represents shares of Class A Common Stock of Hagerty, Inc. (the "Issuer") underlying Restricted Stock Units ("RSUs") acquired by the Reporting Person under the Issuer's 2021 Equity Incentive Plan. The RSUs vest on April 1, 2027, subject to the Reporting Person's continued service with the Issuer, with exceptions for death or disability.

Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of restricted stock units ("RSUs") pursuant to various RSU award agreements.

This transaction was executed in multiple trades at prices ranging from $10.45 to $10.92. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

The reported sale was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 15, 2025.

This transaction was executed in multiple trades at prices ranging from $12.30 to $12.67. The price reported above reflects the weighted average purchase price. The Reporting Person hereby undertakes to provide upon request to the SEC staff, the Issuer or a security holder of the Issuer full information regarding the number of shares and prices at which the transaction was effected.

The Reporting Person is the sole member of Quadrifoglio Holdings LLC and has voting and investment discretion with respect to the securities held of record by Quadrifoglio Holdings LLC. The Reporting Person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest therein.

Quadrifoglio Holdings LLC received 2,044,272 Common Units of The Hagerty Group, LLC (the "Restricted Units") pursuant to the terms of that certain Contribution and Exchange Agreement, dated as of August 9, 2022, among the Issuer and the parties thereto. The Restricted Units are subject to exchange restrictions that release in five equal installments on April 1st of each year (which began on April 1, 2023) (all Restricted Units that have been released from the exchange restrictions are referred to herein as the "Released Units"). The reported transaction reflects the conversion of 50,000 Released Units owned by Quadrifoglio Holdings LLC into shares of the Issuer's Class A Common Stock pursuant to that certain Exchange Agreement, dated as of August 9, 2022, by and among the Issuer and the parties thereto (the "Conversion"). After the Conversion, Quadrifoglio Holdings LLC owns 775,213 Released Units.

The Reporting Person is the sole member of Quadrifoglio Holdings LLC and has voting and investment discretion with respect to the securities held of record by Quadrifoglio Holdings LLC. The Reporting Person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest therein.