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Larry Ellison is preparing to sell as many as 50 million Oracle shares, worth about $7.5 billion at the current price, under a trading plan he adopted in late June that runs through Oct. 24.
The Financial Times reported the plan, which appears in Oracle's filings with the Securities and Exchange Commission. A Rule 10b5-1 plan is an arrangement executives set up in advance, specifying how many shares will be sold and when, so that the sales cannot be read as acting on inside information.
What makes it unusual is that Ellison almost never sells.
The Oracle co-founder has held roughly 1.16 billion shares for years, about 40% of the company, and has funded his spending by borrowing against them rather than realising gains. Selling would trigger capital gains tax on a position with an effectively zero cost basis. Borrowing does not. Regulatory filings showed he had sold no Oracle shares at all during the preceding year.
Oracle made a specific exception for him. When the company banned directors, executives and their families from pledging shares as collateral in 2018, it wrote a carveout for its chairman, and its governance committee has repeatedly told shareholders the arrangement poses no material risk. Filings have shown between 277 million and 346 million of his shares pledged against personal borrowing.
The problem with borrowing against shares is what happens when they fall.
Oracle has fallen roughly 64% from its September 2025 peak, when the stock briefly traded above $345 as investors bought into its artificial intelligence cloud business. It closed near $150 last week. S&P has cut the company to one notch above junk, and it carries about $117 billion of outstanding bonds against heavy spending on AI data centres.
Ellison's own position moved with it. He became the world's richest person for a day on Sept. 10, 2025, at close to $393 billion, only the second person after Elon Musk to pass $400 billion on some measures. Forbes put him at $201 to $203 billion in early 2026, sixth in the world.
A separate commitment has tightened the position further.
Ellison personally guaranteed $40.4 billion of the equity financing for the $110 billion merger between Paramount Skydance, run by his son David, and Warner Bros. Discovery. The Ellison Family Trust, which holds the 1.16 billion Oracle shares, provides a $45.7 billion equity backstop. He made that commitment when Oracle was near its high.
Twelve state attorneys general sued to block the merger in July, despite approval from the Justice Department in June. A $7 billion termination fee is at stake if the deal collapses.
The sale itself is small against what he owns. Fifty million shares is roughly 4% of his holding, and it does not change who controls Oracle.
The signal is what investors will weigh. Ellison has sold Oracle stock before, mostly to exercise options and cover tax, and one estimate puts his cumulative net proceeds from sales at about $5.1 billion over his entire career. Doing $7.5 billion inside four months would exceed everything that came before it.
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