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HGTY Hagerty, Inc. Insider Trading

Latest: Director Bought $99K of Shares · May 2026

Multiple insiders have been active at Hagerty, Inc. (HGTY): 4 distinct insiders account for 6 buy filings and 16 sell filings as of May 2026. Its highest-significance filing in the last 90 days: Director Kuczinski Anthony J bought $99K, transaction dated May 2026.

22 filings analyzed · Latest 2026-05-19

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Buys
6
Sells
16
Insiders
4
Direction
Net selling

Hagerty, Inc. leadership

General Counsel
Diana Chafey — Chief Legal Officer and Corporate Secretary
Chair
McKeel Hagerty — Chairman of the Board

Historically, high-priority insider buys have outperformed the S&P 500 by a median ~2% over the 30 days after the trade — the edge is concentrated in that first month (n ≈ 5,579, 2024-2026). Past results don't predict the future. How we measure this ↗

May 2026
2026-05-19
high
9,500 shares
$99,370
@ $10.46
Significance 7

Director Kuczinski buys 9,500 shares of HGTY at $10.46 on 2026-05-15; stock at $11.05, down 21.1% from 52-week high

Kuczinski purchased 9,500 shares at $10.46, increasing his holdings by 16.1% to 68,648 shares. His prior 5 purchases at HGTY all delivered positive 90-day returns (ranging from +2.5% to +15.7%), establishing a consistent pattern of well-timed entry points at this ticker. The current share price of $11.05 sits significantly below the 52-week high of $14.00, though recent momentum shows +2.0% gain over 30 days. The company reports $311.8M quarterly revenue with +21.4% annual growth, but faces current profitability headwinds at -$12.7M net income. This purchase occurs amid price weakness relative to the 52-week range, following a demonstrated history of accurate timing at this specific ticker.

March 2026
2026-03-13
high
4,000 shares
$38,000
@ $9.50
Significance 6

Director Kuczinski buys 4,000 shares of HGTY at $9.50; 5 prior HGTY buys all well-timed at 90-day mark, now -21.2% over 90 days

Kuczinski Anthony J (Director) purchased 4,000 shares at $9.50 on 2026-03-12, increasing his holdings to 47,277 shares (+9.2% vs pre-transaction). His prior trades at HGTY show a consistent pattern: 4 of 4 measurable prior buys were well-timed at the 90-day mark (with 90-day returns of +9.6%, +13.0%, +12.8%, and +2.7%). However, the stock has declined -21.2% over the last 90 days and trades at $10.23 (−26.0% from the 52-week high of $13.82), so this recent purchase entered a downtrend. The company fundamentals remain solid—$379,994,000.00 in latest-quarter revenue, $46,171,000.00 net income, and +21.4% annual revenue growth—but the timing relative to recent price action differs markedly from his historical pattern of catching bottoms before meaningful recoveries.

2026-03-04
high
15,000 shares
$160,800
@ $10.72
Significance 7

Director Kuczinski buys 15,000 HGTY shares at $10.72; stake rises 53.0% to 43,277 shares amid price decline

Director Anthony J Kuczinski purchased 15,000 shares at $10.72 on 2026-03-03, increasing his holdings by 53.0% to 43,277 shares. The transaction occurs with the stock trading 21.7% below its 52-week high of $13.82 and down 14.7% over the prior 30 days. His prior five purchases at HGTY have shown consistent positive 90-day outcomes (ranging from +2.7% to +13.0%), and he has executed 5 of 5 prior buys with positive returns at the 90-day mark. Hagerty's fundamentals remain solid with $380.0M quarterly revenue, $46.2M net income, and 21.4% annual revenue growth, though the stock's recent weakness may have created an entry opportunity for the director's accumulation.

January 2026
2026-01-27 10b5-1 Plan
medium
President, Hagerty Marketplace
50,000 shares
$620,500
@ $12.41
Significance 5

HGTY President Ahn Kenneth sold 50,000 shares at $12.41 on 2026-01-26, holding zero shares post-transaction; fifth sale in 20 days.

Ahn Kenneth, President of Hagerty Marketplace, sold 50,000 shares at $12.41 on 2026-01-26 totaling $620,500.00. This transaction eliminates his open-market equity stake in HGTY, representing the fifth discretionary sale in the past 20 days (prior sales occurred on 2026-01-20, 2026-01-12, 2026-01-09, 2026-01-07, and 2026-01-06). The sale occurred at a price slightly above the current market ($12.14), placing the trade within 2% of the 52-week high ($13.82) and well above the 52-week low ($8.34). Hagerty's fundamentals remain solid—annual revenue growth of +20.0%, net income of $46.2M, and a P/E of 32.81—but the rapid, sequential liquidation of equity holdings by a senior executive over three weeks warrants attention as a potential signal of changing capital allocation priorities or personal financial circumstances rather than fundamental distress.

2026-01-22 10b5-1 Plan
medium
President, Hagerty Marketplace
50,000 shares
$627,500
@ $12.55
Significance 4

Kenneth Ahn sells 50,000 HGTY shares at $12.55; completes conversion and liquidates Table I position to zero

Kenneth Ahn, President of Hagerty Marketplace, sold 50,000 shares at $12.55 on 2026-01-20, resulting in zero remaining Table I shares post-transaction. This sale is part of a conversion transaction (derivative securities conversion), meaning Ahn's actual economic position resides in Form 4 Table II, which is not yet populated in the database—the zero holdings shown here reflect only the conversion and liquidation of Table I shares, not a complete exit from the company. The timing is noteworthy: this sale occurred just 8 days after a prior sale on 2026-01-12, continuing a pattern of five consecutive sales within a 16-day window (2026-01-05 through 2026-01-20), all executed below the 52-week high of $13.82. While Hagerty shows strong fundamentals with $380.0M revenue, +20.0% annual growth, and $46.2M net income, the rapid-fire sales sequence and current price of $12.81 (−7.3% from the 52-week high, −4.1% over 30 days) merit tracking whether this clustering reflects scheduled derivative settlement or discretionary positioning.

2026-01-13 10b5-1 Plan
medium
President, Hagerty Marketplace
51,350 shares
$660,888
@ $12.87
Significance 6

HGTY President Ahn Kenneth sells 51,350 shares in 2 transactions (Jan 9-12) for $660,887.50; now holds zero common shares.

Kenneth Ahn, President of Hagerty Marketplace, executed 2 separate sales on 2026-01-09 and 2026-01-12, selling 1,350 shares at $13.25 and 50,000 shares at $12.86, respectively, for a combined total of $660,887.50 at a blended average price of $12.87. The stock currently trades at $12.69, near the lower end of its 52-week range ($8.34–$13.82) and down 8.2% from its 52-week high, though up 4.4% over 90 days. This filing shows conversion of derivative securities (Form 4 Table II not yet populated), so his full position extends beyond common shares; the zero common-share balance does not represent a complete exit from his Hagerty holdings. His prior sales at HGTY (4 trades since late December) show a pattern of sequential reductions, though timing outcomes remain unmeasurable given the recent dates of those transactions.

2026-01-07 10b5-1 Plan
medium
President, Hagerty Marketplace
200,000 shares
$2,565,685
@ $12.83
Significance 6

Hagerty President Ahn Kenneth sold 200,000 shares across 3 transactions (Jan 5-7, 2026) for $2,565,684.61 via pre-arranged 10b5-1 plan.

Kenneth Ahn, President of Hagerty Marketplace, executed 3 separate sales totaling 200,000 shares for $2,565,684.61 on January 5-7, 2026, at prices ranging from $12.79 to $13.08 per share with a blended average price of $12.83. This activity was conducted pursuant to a pre-arranged 10b5-1 trading plan adopted on 2025-09-15, meaning the sales were scheduled and non-discretionary rather than responsive to current market conditions. The Form 4 indicates derivative securities held in Table II remain to be populated, indicating this represents a conversion of derivative holdings rather than a complete position liquidation. Investors should review the full derivative holdings table when available to assess the executive's total remaining stake in the company.

December 2025
2025-12-17 10b5-1 Plan
medium
President, Hagerty Marketplace
100,000 shares
$1,280,000
@ $12.80
Significance 6

Hagerty President Kenneth Ahn sells 100,000 (100.0K shares) for $1,280,000.00; holds derivative securities post-transaction

Kenneth Ahn, President of Hagerty Marketplace, sold 100,000 (100.0K shares) at $12.80 on 2025-12-15, resulting in holdings of zero shares in Table I. However, this filing contains a conversion of derivative securities—the insider's actual position includes derivative holdings in Table II (not yet populated in our database), and this should not be characterized as a complete exit from the company. The transaction occurred near the stock's 52-week range ($8.34–$13.73) and slightly above the current price of $12.76. Hagerty's fundamentals show strong revenue growth of +20.0% year-over-year with net income of $46,171,000.00 ($46.2M), though the company trades at a P/E of 34.49 and commands a market cap of $4,415,499,326.92 ($4.4B). The disposal of this specific equity batch warrants review in the context of the insider's full derivative position to determine its significance relative to total economic exposure.

October 2025
2025-10-16 10b5-1 Plan
medium
91,307 shares
$1,097,881
@ $12.02
Significance 6

Director Kauffman sells 91,307 shares across 3 trades (Oct 14-16) for $1,097,881.46; recent HGTY sales show positive 30d returns.

Robert I. Kauffman, Director, executed 3 separate sales totaling 91,307 shares for $1,097,881.46 over three consecutive trading days at an average price of $12.02, reducing his holdings by -8.5% from 1,079,049 to 987,742 shares. The current stock price of $11.44 is -12.1% from the 52-week high and down -7.8% over the past 30 days. Notably, Kauffman's 5 most recent prior sales at HGTY (all within the past 2 months) each showed positive 30-day returns ranging from +6.0% to +40.4%, indicating the stock rose after each sale. The company remains fundamentally strong with $368.7M quarterly revenue, 20.0% annual growth, and positive net income of $47.2M, though trading at a P/E of 39.45 suggests elevated valuation. The consistent pattern of positive 30-day post-sale returns across his recent HGTY transactions may reflect general market strength rather than insider-driven timing signals.

September 2025
2025-09-08
medium
1,000 shares
$11,620
@ $11.62
Significance 6

Director Kuczinski bought 1,000 shares of HGTY at $11.62; holds 28,277 shares post-transaction. Stock up 25.4% in 90 days, 4 of 4 prior buys well-timed.

Director Anthony J Kuczinski purchased 1,000 shares at $11.62, bringing his holdings to 28,277 shares. The stock is trading at $12.08, near the 52-week high of $12.08, following a 25.4% rally over the past 90 days. Notably, Kuczinski's prior trade history at Hagerty shows a strong pattern: all 4 previous buys at this ticker were well-timed on the 90-day horizon (each followed by positive returns ranging from +2.7% to +13.0%), suggesting the director has a track record of accumulating shares before periods of appreciation. The current buy occurs as the stock approaches its 52-week high, and the company reports strong fundamentals with $368.7M in quarterly revenue, $47.2M net income, and 20.0% annual revenue growth. The pattern of consistent accumulation by a director with demonstrated timing accuracy warrants monitoring to see if the current trajectory continues or if the stock's proximity to recent highs signals a different market phase.

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