Deere CEO Executes Large Sale of 41,472 Shares Under Pre-Announced 10b5-1 Plan

CEO Executes Stock Options and Sells Equivalent Shares, Realizes $20.9 Million

John C. May II, chairman and chief executive officer of Deere & Co (DE), exercised market-priced stock options on January 8, 2026, acquiring 41,472 common shares at $254.83 per share and immediately sold the same number of shares in multiple transactions at prices ranging from $500.46 to $503.35. The transactions generated approximately $20.9 million in cash (about ₩29.26 billion). According to the company, the trades were conducted under SEC Rule 16b-3 to facilitate liquidity and cover tax obligations, emphasizing that these were pre-planned disposals rather than directional bets.

## Maintains Stake Valued at About $73.2 Million – Not a Full Exit Signal

Despite the January sale, May still holds a substantial investment in Deere & Co. As of the latest filings, he owns 145,861 shares in total (117,970 directly and 27,891 indirectly through an SLAT trust), plus 19,950 restricted stock units (RSUs). At an estimated share price of $502, his direct and indirect holdings are worth approximately $73.2 million (around ₩102.48 billion). While the sale generated significant cash, experts note that the remaining equity stake, unexercised options and RSUs suggest it’s premature to interpret the move as a loss of confidence by management.

Sale Foreshadowed in June 2025 Form 144 Under 10b5-1 Plan

Investors had advance notice of this sale under a Form 144 filing dated June 20, 2025. In that filing, May disclosed a plan to sell 41,472 Deere & Co common shares around January 8, 2026, at an estimated value of $20.8 million (about ₩29.12 billion), to be executed through Fidelity Brokerage Services. The January 8 transactions were carried out under this pre-arranged 10b5-1 plan, distinguishing them from opportunistic “insider” sales.

Investor Perspectives: Liquidity and Tax Planning vs. Psychological Impact

From a market standpoint, two interpretations coexist: - Positive view: A scheduled 10b5-1 sale driven by tax and liquidity needs, signaling no fundamental concerns. - Cautionary view: Converting over $20 million into cash at once may weigh on some investors’ sentiment, particularly amid worries about economic slowdown and capital spending cycles, potentially adding volatility.

Future Checkpoints: Follow-on Sales, Compensation Structure, and Guidance Linkage

Analysts recommend monitoring:

• Any further sales by May or other executives.
• Changes in the management incentive structure and equity ownership.
• Deere & Co’s medium- to long-term results and guidance trends.

If May continues to retain a significant stake while only exercising options as part of a routine compensation cycle, the impact may be limited. However, a series of similar-sized sales or coordinated disposals by other executives could reinforce narratives around risk aversion or a potential peak in performance. Investors should track new 10b5-1 registrations, quarterly order and margin guidance, and related disclosures.