Larry Ellison has spent most of the 21st century not selling Oracle stock. That changed on June 22, 2026, when he adopted a Rule 10b5-1 trading plan that would allow him to offload up to 50 million shares of Oracle through October 24, 2026.
When the plan was filed, those shares were worth roughly $175 each, putting the potential total near $8.75B. Oracle’s stock has since pulled back to around $150, trimming the maximum expected proceeds to approximately $7.5B.
Why this is unusual
To understand why this matters, some context on Ellison’s track record: the largest single share sale he has made this century was 25,000 shares. His preferred move has been to borrow against his holdings rather than convert them to cash, a common strategy among ultra-wealthy founders who want liquidity without triggering a taxable event or sending a signal to the market.
This plan involves up to 50 million shares. That is a very different kind of number.
