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 sell stock at predetermined prices or on a fixed schedule without running afoul of insider trading rules. Once the plan is in place, the trades can execute automatically, even if Ellison is deep inside a sensitive product decision or a board meeting about unreleased financials.

The Oracle backdrop is complicated right now

The timing of the disclosure lands alongside some notable turbulence inside Oracle itself. The company announced an additional $700M in restructuring and severance costs, driven primarily by its pivot toward AI infrastructure and the workforce reductions that come with reorganizing around new priorities.

The share price tells part of that story. Oracle reached peaks in 2025, and the stock has retreated from those highs. Investor concerns about spending levels and balance sheet leverage have applied steady downward pressure, which means Ellison’s 50 million shares are now worth materially less than they were when he filed the plan.

That gap matters because a 10b5-1 plan does not guarantee sales. It establishes conditions under which sales may occur. If Oracle’s stock continues sliding, some of those conditions may never trigger, and the full $7.5B to $8.75B in potential proceeds may never materialize.

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