Chafey Diana 4

What Happened
Diana Chafey, Chief Legal Officer of Hagerty, had 23,742 restricted stock units (RSUs) vest on April 1, 2026 (reported as an acquisition, code A). To cover tax withholding, 4,833 shares were surrendered/disposed at $10.66 per share (code F) for a withholding amount of $51,520. Separately, on April 2, 2026 she purchased 1,165 shares through Hagerty’s Employee Stock Purchase Plan (ESPP) at $10.13 per share for $11,801 (code A).

Key Details

• Transaction dates and prices:
  • 2026-04-01: 23,742 RSU shares vested (acquired at $0.00 per share for reporting).
  • 2026-04-01: 4,833 shares withheld for taxes at $10.66 — total $51,520 (disposition for tax withholding).
  • 2026-04-02: 1,165 ESPP shares purchased at $10.13 — total $11,801.
• Shares owned after transaction: Not specified in this Form 4.
• Notable footnotes:
  • F1: RSUs vest annually through April 1, 2029, subject to continued service (and usual exceptions).
  • F2: The 4,833-share disposition represents shares withheld to satisfy tax obligations on vesting.
  • F3/F4: ESPP purchase covers Oct 1, 2025–Mar 31, 2026 offering; per-share price was 95% of the April 1, 2026 closing price.
• Timeliness: Filing dated 2026-04-03 for transactions on 4/1–4/2 appears timely (Form 4 due within two business days).

Context
This filing shows routine RSU vesting and tax-withholding (common for employees) plus an ESPP purchase — the latter is a direct purchase by the insider and is generally viewed as a more informative bullish action than routine withholding. No option exercises or sales for cash beyond the tax-withholding disposition are reported.