Oracle is betting big on AI and debt. Now Larry Ellison could cash in $7.5 billion

Larry Ellison has adopted a trading plan that could allow him to sell as many as 50 million Oracle shares, worth about $7.5 billion at the current price, CNBC reported. Oracle's aggressive push into artificial intelligence infrastructure is putting pressure on its finances even as the company's cloud business accelerates.

Larry Ellison adopted the trading plan on June 22, and it will run until October 24, according to a regulatory filing published on Friday. The move comes as Oracle takes on substantial debt to fund the construction of large-scale data centres for AI customers, while also cutting costs and reducing its workforce.

Ellison controls more than 40% of Oracle, according to FactSet. If he sells all 50 million shares covered by the plan, he would still hold about 1.1 billion shares in the company he co-founded in 1977.

The Oracle founder's potential stock sale would therefore come at a time when his company is committing heavily to AI infrastructure while his own financial interests extend beyond the software business.

Oracle's AI push comes with rising debt and job cuts

Oracle has become a major AI infrastructure provider, using its established software business to fund a costly expansion of cloud capacity for customers such as OpenAI.

The investment has increased pressure on the company's finances. Oracle's restructuring costs are now estimated at about $2.8 billion, largely due to severance payments from massive job cuts, according to the filing.

Oracle has already accrued about $2.1 billion, with the remaining $700 million reflecting additional actions it expects to take.

Oracle has also been cutting jobs as it seeks to reduce costs and preserve margins. The company had about 49,000 employees in the US and roughly 92,000 internationally at the end of May, down by 21,000 from a year earlier.

Oracle revenue jumps 121%

Oracle's financial pressure comes alongside rapid growth in its AI-related cloud business.

Oracle's cloud business grew 121% from a year earlier in its latest results, beating analysts' expectations. The company has been investing heavily in AI data centres as it expands its cloud business.

The expansion, however, has required big borrowings, contributing to investor concerns. Oracle's shares have fallen roughly 20% this year.

Why Ellison's potential Oracle sale is unusual

The size of the proposed sale stands out against Larry Ellison's historical approach to his Oracle holdings.

Since the beginning of this century, Ellison has not sold more than 25,000 Oracle shares at any one time, according to FactSet. The new plan therefore represents a significant departure in scale, although it does not require him to sell the entire 50 million shares.

Ellison, 82, would continue to hold a substantial stake even if all the shares covered by the plan were sold.

Ellison steps back from Oracle earnings spotlight

The potential share sale also comes as Ellison has become less prominent in Oracle's quarterly earnings calls.

Ellison remained the company's public face for decades after stepping down as chief executive in 2014. He regularly featured on earnings calls, with occasional absences, including one in September 2013 when he was attending the America's Cup yacht race.

That changed this year after Oracle appointed Clay Magouyrk and Mike Sicilia as co-chief executive officers as part of its shift towards cloud infrastructure.

Oracle founder's wider financial interests

Larry Ellison has also been a major financial backer of his son David Ellison's business ventures.

He helped finance David Ellison's 2025 merger of Skydance with Paramount and has also backed Paramount Skydance's reported $110 billion bid for Warner Bros. Discovery.