Larry Ellison Cancels $7.5 Billion Oracle Share Sale Plan

In a surprising move, Larry Ellison, the founder and chief executive of Oracle (NYSE:ORCL), has cancelled a Rule 10b5-1 trading plan that would have allowed him to sell up to 50 million shares, a transaction CNBC valued at roughly $7.5 billion at the time of reporting. The cancellation came just one day after the plan was publicly disclosed, and no shares have been sold under the arrangement.

Quick Read

• Ellison abandoned a $7.5 billion sale of 50 million Oracle shares without selling one.
• The cancellation occurred one day after the plan’s existence was disclosed in a regulatory filing.
• Ellison’s net worth has fallen by approximately $200 billion over the past year, dropping him from the second‑richest person to seventh.
• Oracle’s latest quarter saw $28 billion in capital expenditures and negative $5 billion free cash flow, despite a $664 billion AI cloud backlog.
• A new report from 24/7 Wall St. names the ten best stocks to buy now, and Oracle is not among them.

Sequence and Timing

The 10b5-1 plan was adopted on June 22 and was scheduled to run through October 24, according to CNBC. Its existence was revealed in a filing on September 11, 2026. The next day, September 12, Oracle announced that Ellison had cancelled the plan. No reason was provided for the withdrawal, and no shares were sold under the arrangement.

Trading plans are typically set up for tax, estate, or liquidity purposes, and companies rarely disclose the motivations behind their adoption or cancellation. In this case, Oracle’s silence has left analysts to speculate on the reasons.

Oracle’s Stock and the Debt Story Behind It

Oracle’s stock has experienced a steep decline. On September 14, 2026, the shares traded at $141.61, down 5.77% in the session and 10.81% over the previous week. Year‑to‑date, the stock is off 26.64%, and over the trailing twelve months it has fallen 53.48%.

The drop coincides with Oracle’s aggressive shift from a legacy software vendor to an AI infrastructure provider. In its Q1 fiscal 2027 results, filed on September 10, the company reported cloud infrastructure revenue up 121% and remaining performance obligations of $664 billion. However, the transformation comes at a cost: capital expenditures of $28 billion in a single quarter, free cash flow of negative $5 billion, and a completed $20 billion at‑the‑market equity issuance.

Forbes contributor Jim Osman noted on September 12 that Oracle continues to burn cash amid its AI spending and capital raises. CFO Hilary Maxson told analysts that infrastructure projects are expected to achieve a free cash flow conversion ratio of roughly 100% to post‑tax EBITDA once they ramp, but she did not commit to a date for a return to positive free cash flow.

A Fortune Tied to One Ticker

Ellison, 82, founded Oracle in 1977 and still controls more than 40% of the company. His wealth is therefore tightly linked to Oracle’s stock performance. In September 2025, Forbes reported he became only the second person ever worth more than $400 billion, driven by an AI‑fueled surge in Oracle’s share price. Twelve months later, the Bloomberg Billionaires Index placed his net worth at $204 billion, ranking him seventh globally, a decline of roughly $200 billion.

The concentration of Ellison’s wealth in a single company explains why a share‑denominated 10b5-1 plan of this size attracted attention. Such plans are usually adopted and withdrawn for reasons that issuers rarely disclose, but Oracle provided no explanation in this instance.

Investor Takeaway

The cancellation of Ellison’s trading plan, combined with Oracle’s heavy capital spending and negative free cash flow, signals a period of uncertainty for investors. While the company’s AI cloud backlog is substantial, the path to profitability remains unproven.

For those considering an investment in Oracle, the current environment warrants caution. A recent analysis by 24/7 Wall St. identified the ten best stocks to buy now, and Oracle did not make the list. Investors may want to review the report to understand the alternatives.

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