HENSLEE GREGORY L 4

What Happened
Gregory L. Henslee, Chairman of the Board and a director of O'Reilly Automotive (ORLY), received a restricted share award of 4,305 shares on 2026-01-29 valued at $98.85 per share (total $425,549). Following the award vesting-related tax obligation, 1,461 shares were withheld/disposed on 2026-01-30 at an implied value of $98.41 per share (total ~$143,777) to satisfy payroll tax withholding. The primary event is an award (not an open-market purchase or voluntary sale); the withholding is a routine tax-related disposition.

Key Details

• Transaction dates and values:
  • 2026-01-29: Award of 4,305 restricted shares @ $98.85 each = $425,549 (code A).
  • 2026-01-30: 1,461 shares withheld to satisfy payroll taxes @ $98.41 each = $143,777 (code F).
• Shares owned after transactions (as reported): Includes 4,305 unvested restricted shares plus 237,180 shares held directly by Mr. Henslee. Additional holdings reported: 74,897 shares in the company 401(k) and 116,706 shares held as trustee of a GRAT. Total reported beneficial ownership across these accounts: 433,088 shares (includes unvested award).
• Notable footnotes:
  • The 4,305-share award vests in one equal annual installment on January 29, 2027 (F1).
  • The 1,461-share disposition represents shares withheld to satisfy payroll tax withholding upon vesting (F2).
• Filing: Form filed 2026-02-02 reporting the 2026-01-29/30 transactions (no late-filing flag provided).

Context
Restricted share awards are compensation, not open-market purchases; withholding shares to satisfy tax obligations is a common administrative step and does not necessarily indicate a change in the insider's view of the company's stock. The award is unvested until the stated vesting date (Jan 29, 2027), so the recipient cannot freely sell those shares until they vest.