AUSTIN, TX – September 13, 2026 (STL.News) Oracle Corp. co-founder Larry Ellison has canceled a trading plan that could have allowed him to sell as many as 50 million shares of Oracle stock, eliminating a potential multibillion-dollar insider sale at a pivotal moment for the technology giant and its massive artificial intelligence expansion.
At Oracle’s Friday closing price of $150.28, the maximum number of shares covered by the plan would have been worth approximately $7.5 billion.
Perhaps more significant for investors, Oracle said no shares were sold under the plan before Ellison canceled it and that he currently has no other plans to sell his Oracle holdings.
The decision comes as Oracle, NYSE: ORCL, attempts one of the largest infrastructure expansions in its history, driven by enormous demand for computing capacity required to train and operate artificial intelligence models.
Oracle’s business is growing rapidly.
So is its spending.
Those two competing realities have become central to the debate surrounding Oracle shares, which have fallen more than 20% during 2026 despite extraordinary growth in the company’s cloud infrastructure business.
Ellison’s decision therefore removes one potentially negative issue hanging over Oracle stock: the possibility that its billionaire co-founder and largest shareholder could unload tens of millions of shares while investors are already questioning the financial cost of Oracle’s AI ambitions.
Ellison’s Plan Could Have Sold 50 Million Shares
Ellison adopted the Rule 10b5-1 trading arrangement on June 22, according to Oracle’s disclosure.
The plan could have permitted the sale of as many as 50 million Oracle shares and was scheduled to terminate Oct. 24, subject to provisions allowing earlier termination.
Oracle announced Saturday that Ellison had canceled the arrangement.
None of the shares authorized under the plan had been sold.
Oracle also said Ellison has no other plans to sell Oracle stock.
The company did not provide an official explanation for the cancellation.
That distinction is important.
The Financial Times reported that a person close to Ellison said the billionaire believes Oracle shares are undervalued. However, Oracle itself has not publicly attributed the cancellation to valuation, and investors should not automatically interpret the decision as an official declaration by Ellison that Oracle stock is undervalued.
Nevertheless, canceling the sale eliminates the possibility of selling up to 50 million shares through that trading arrangement.
What Is a Rule 10b5-1 Trading Plan?
Rule 10b5-1 plans are commonly used by corporate executives and other insiders to establish predetermined arrangements for buying or selling company securities.
They can allow executives to establish trading instructions before transactions occur, potentially reducing concerns that subsequent trades were based on material nonpublic information.
The existence of such a plan does not necessarily mean an executive has lost confidence in a company.
Executives frequently sell shares for diversification, taxes, estate planning, charitable giving or other personal financial reasons.
Likewise, cancellation of a plan does not necessarily predict that a stock will rise.
But the sheer size of Ellison’s potential transaction made this particular arrangement noteworthy.
Fifty million Oracle shares represented approximately $7.5 billion at Friday’s closing price.
Ellison is no ordinary Oracle insider.
He co-founded the company that became Oracle in 1977 and remains executive chairman and chief technology officer. Reuters reported that Ellison remains Oracle’s largest shareholder, controlling more than 38% of the company.
That means his financial fortunes remain extraordinarily closely tied to Oracle.
Oracle Shares Have Struggled in 2026
The cancellation comes after a difficult year for Oracle shareholders.
Oracle shares closed Friday at $150.28 and have declined more than 20% during 2026.
The decline creates an unusual contrast.
Oracle’s underlying cloud business is expanding at rates normally associated with much smaller technology companies.
But building enough data-center capacity to satisfy AI customers requires enormous amounts of capital.
That has forced investors to confront a fundamental question:
How much will Oracle have to spend today to generate the enormous AI revenues it expects tomorrow?
Oracle’s fiscal first-quarter results released Sept. 10 illustrate both sides of that equation.
Oracle Revenue Reaches $19.3 Billion
Oracle reported fiscal first-quarter 2027 revenue of approximately $19.3 billion, an increase of 30% from the previous year.
Total cloud revenue increased 62% to $11.6 billion.
Oracle Cloud Infrastructure revenue was particularly impressive.
Infrastructure-as-a-Service revenue reached approximately $7.4 billion, representing year-over-year growth of 121%.
Cloud application revenue increased 10% to approximately $4.2 billion.
Meanwhile, traditional software revenue declined 3% to $5.5 billion as Oracle customers continued migrating from on-premises software toward cloud products.
Hardware revenue increased 15% to approximately $800 million, while services revenue increased 5% to approximately $1.4 billion.
Oracle also reported GAAP operating income of approximately $6.7 billion, up 57%.
GAAP net income available to common shareholders reached approximately $4.7 billion, increasing 60%.
GAAP earnings per share climbed 55% to $1.56, while non-GAAP earnings per share increased 30% to $1.92.
Those are powerful operating numbers.
But another number may be even more important to Oracle’s long-term investment story.
Oracle’s Backlog Hits $664 Billion
Oracle reported remaining performance obligations, commonly called RPO, of approximately $664 billion.
That represents contracted revenue that generally has not yet been recognized.
RPO increased approximately $209 billion from a year earlier.
Oracle said it booked more than $30 billion of additional AI cloud contracts during the fiscal first quarter alone.
That backlog provides investors with extraordinary visibility into potential future revenue.
Oracle says demand for its AI cloud training and inferencing services continues to grow faster than the company can supply capacity.
Since the end of its previous fiscal quarter, Oracle said it delivered more than 300,000 graphics processing units, or GPUs, to AI cloud customers.
Oracle also delivered approximately 850 megawatts of additional data-center capacity during the quarter.
In other words, Oracle’s problem is not necessarily finding customers.
Its challenge is building enough infrastructure to serve them — and financing that construction without placing excessive pressure on its balance sheet or shareholders.
The $90 Billion to $95 Billion Spending Question
Oracle expects fiscal 2027 capital expenditures of approximately $90 billion to $95 billion, according to current company guidance and reporting surrounding its quarterly results.
That level of spending demonstrates how dramatically the economics of the technology industry are changing because of artificial intelligence.
AI data centers require enormous investments in GPUs, servers, networking equipment, power infrastructure, cooling systems, buildings and electrical capacity.
Oracle is competing for that business against some of the world’s largest, best-capitalized corporations.
The opportunity could be enormous.
So could the financial risk if expected AI demand fails to generate sufficient returns on those investments.
Oracle’s latest cash-flow numbers illustrate the issue.
Oracle Generated $23 Billion — And Still Burned Cash
Oracle generated a record $23 billion in operating cash flow during its fiscal first quarter, up 184%.
Yet free cash flow for the quarter was approximately negative $5 billion because of the company’s massive investment in cloud infrastructure.
That combination deserves attention.
A company producing $23 billion in operating cash flow in a single quarter would ordinarily appear to have tremendous financial flexibility.
Oracle does.
But the scale of its infrastructure program is so enormous that even record operating cash generation has not prevented negative free cash flow.
This is arguably one of the most important numbers for investors evaluating Oracle.
The company’s AI strategy doesn’t depend solely on signing customers.
Oracle must convert hundreds of billions of dollars of contracted business into profitable revenue while financing the physical infrastructure required to provide those services.
Oracle Already Raised $20 Billion by Selling Stock
Another important element of the Ellison story is this.
While Ellison canceled his personal stock-sale plan, Oracle itself has already been issuing shares to finance its expansion.
During the first fiscal quarter, Oracle completed the sale of approximately $20 billion of common stock before commissions through an at-the-market equity program.
Oracle described the offering as part of its previously disclosed capital investment program.
That creates an interesting juxtaposition.
Oracle is raising enormous amounts of capital to finance AI infrastructure.
Meanwhile, its largest individual shareholder has canceled a plan to sell another 50 million shares from his personal holdings.
These transactions are fundamentally different — Oracle’s equity issuance raised money for the corporation, while Ellison’s planned transactions would have involved his personally owned shares.
But both matter when evaluating the supply of Oracle stock entering the market.
Removing a Potential Stock Overhang
Large planned insider sales sometimes create what investors describe as a stock “overhang.”
The term does not mean the shares will necessarily decline.
Instead, investors know that a substantial block of shares could potentially be offered for sale.
With Ellison’s plan canceled before any shares were sold, that particular potential source of selling pressure has disappeared.
The development could therefore improve investor sentiment around Oracle, even though it changes nothing directly about the company’s revenue, earnings, debt, or AI contracts.
Investors will ultimately determine how much significance to attach to Ellison’s decision when Oracle shares resume trading.
Oracle Raises Its Outlook
Oracle’s latest results also included stronger guidance.
The company now expects fiscal 2027 revenue of at least $90 billion.
Oracle also raised its full-year non-GAAP earnings-per-share outlook to approximately $8.10.
For the fiscal second quarter, Oracle expects total revenue growth between 30% and 34%.
Total cloud revenue is expected to increase by approximately 65% to 71% in U.S. dollars.
Oracle expects second-quarter non-GAAP earnings of approximately $1.85 to $1.93 per share.
The company has therefore entered an unusual period in which operational growth is accelerating while capital requirements are simultaneously becoming more demanding.
Ellison Remains Deeply Tied to Oracle
Ellison’s continuing ownership is another reason the canceled sale deserves attention.
Reuters reported that he still owns more than 38% of Oracle.
That makes his economic exposure to Oracle enormous.
The Financial Times has separately reported that hundreds of millions of Ellison’s Oracle shares have been pledged as collateral for personal borrowing.
Pledged shares are not the same thing as sold shares, and investors should distinguish between the two.
But the disclosure demonstrates how closely Ellison’s broader personal financial position remains connected to Oracle’s market value.
The AI Opportunity Is Enormous — So Is the Execution Risk
Oracle’s investment case increasingly hinges on whether the company can turn its enormous AI backlog into profitable, cash-generating business.
The bullish argument is straightforward.
Oracle has $664 billion in remaining performance obligations.
Cloud infrastructure revenue is growing at triple-digit rates.
The company continues signing enormous AI contracts.
Demand currently exceeds available capacity.
Management also expects annual revenue of at least $90 billion in fiscal 2027.
The cautious argument is equally straightforward.
Building AI infrastructure is extraordinarily expensive.
Oracle expects tens of billions of dollars in capital expenditures.
Free cash flow was negative $5 billion in the latest quarter, despite $23 billion in operating cash flow.
The company has already raised $20 billion through an equity offering.
And Oracle shares remain sharply lower for 2026 as investors attempt to determine whether future AI profits will justify today’s spending.
Both arguments can be true simultaneously.
Oracle can have extraordinary growth prospects while facing extraordinary financial execution risks.
What Investors Should Watch Next
The cancellation of Ellison’s trading plan does not solve Oracle’s biggest financial questions, but it removes one uncertainty.
Investors no longer have to consider the possibility of as many as 50 million Oracle shares being sold through that specific Ellison trading plan before late October.
Attention can now return to Oracle’s operating performance.
The most important numbers to monitor will be cloud infrastructure growth, conversion of the $664 billion backlog into recognized revenue, capital expenditures, debt and equity financing, operating cash flow and — perhaps most importantly — free cash flow.
Oracle’s transformation from a traditional enterprise software company into one of the world’s major AI infrastructure providers is happening extraordinarily quickly.
Fiscal first-quarter cloud infrastructure revenue increased 121%.
The company added more than $30 billion in AI cloud contracts.
Its backlog reached $664 billion.
Oracle generated $23 billion in quarterly operating cash flow.
Yet the company still reported negative $5 billion of free cash flow because of the tremendous amount of money being poured into infrastructure.
That is the Oracle investment story in miniature.
Demand is enormous.
Growth is enormous.
And the required investment is enormous.
Ellison’s decision to cancel a potential $7.5 billion stock sale does not determine whether Oracle’s AI strategy will succeed.
But as investors intensely scrutinize the financial cost of that strategy, the company’s co-founder and largest shareholder has removed the prospect of one very large insider sale.
For Oracle shareholders, what happens next will depend much less on Ellison’s canceled transaction and much more on whether Oracle can convert one of the technology industry’s largest contracted revenue backlogs into sustainable earnings and, eventually, substantial positive free cash flow.
Sources: Oracle Corp. earnings releases and SEC filings; Reuters; Financial Times.
Investment disclaimer: This article is for informational and news purposes only and does not constitute investment advice, a recommendation to buy or sell securities, or financial advice. Investors should conduct their own research and consult a qualified financial professional before making investment decisions.
