Larry Ellison enters new trading plan to sell up to $8B in Oracle stock

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. Even after any sales under the plan, Ellison would retain approximately 1.1 billion shares, keeping his ownership stake at over 40% of Oracle. A Rule 10b5-1 plan is essentially a pre-scheduled selling program, set up in advance so that executives can sel...