The Oracle CEO Topped Bezos and Dell With a $1.8 Billion Stock Sale Last Quarter

Jeff Bezos made headlines last month by selling hundreds of millions of dollars’ worth of Amazon shares on the day of his wedding. However, his transaction wasn’t the largest insider stock sale of the quarter. That distinction goes to Oracle CEO Safra Catz, who exercised and sold stock options totaling more than $1.8 billion in the second quarter of 2025—surpassing Bezos’ $737 million sale.

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Combined with her first-quarter sales of $706 million, Catz has offloaded $2.5 billion worth of Oracle stock this year, making her the top insider seller so far, according to Washington Service, a firm that tracks executive stock transactions. Her fortune has now grown to $4 billion, according to Bloomberg’s Billionaires Index.

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The second quarter began with market volatility following President Donald Trump’s April 2 “Liberation Day” tariff announcement, which initially sent stocks tumbling. But a pause in those proposals, coupled with renewed enthusiasm for tech stocks, helped drive markets back to record highs by the end of June—right around the time Catz executed her sales through a prearranged trading plan.

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Despite the rally, insider selling overall declined compared to a year earlier. About 6,000 insiders sold roughly $36 billion in shares during the second quarter, down from 9,000 insiders who sold $62 billion in the same period of 2024. Only Catz and Dell Technologies CEO Michael Dell sold over $1 billion in stock. Bezos is expected to keep selling, having filed a plan to unload 25 million Amazon shares—worth around $5 billion—by May 2026. He has continued selling into July.

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Here’s a breakdown of the top 10 insider sellers for the second quarter of 2025, according to Washington Service:

1. Safra Catz – CEO, Oracle Corp.
Catz sold a total of 8.7 million shares valued at $1.83 billion. In June, she exercised and sold 5 million stock options she received under a performance plan, along with other options nearing expiration. Although she frequently exercises and sells options, she still holds about 1.1 million Oracle shares. Oracle declined to comment.

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2. Michael Dell – CEO, Dell Technologies Inc.
Dell sold 10 million shares worth $1.22 billion. Following prior large transactions last fall totaling $2.3 billion, this latest sale brings his recent total to more than $3.5 billion. He now ranks as the world’s 11th-richest person, with a net worth of $136.9 billion. Dell’s recent gains have been fueled by growth in the company’s AI-focused server business. Dell Technologies didn’t comment.

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3. Jeff Bezos – Chair, Amazon.com Inc.
Bezos sold 3.3 million Amazon shares for $736.7 million in June, coinciding with his wedding. He adopted a trading plan in March to sell up to 25 million shares. Though these were his first sales of 2025, he has also donated nearly 930,000 shares to nonprofits this year. Since 2002, Bezos has sold roughly $45 billion in Amazon stock, while buying only one share. Amazon had no comment.

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4. David Baszucki – CEO, Roblox Corp.
Baszucki sold over 7.4 million shares for $630.9 million, capitalizing on a stock surge driven by the success of Roblox’s Grow A Garden game. The sales, executed through a trading plan adopted in late 2024, were conducted through trusts and his family foundation. His net worth now sits at $6 billion. Roblox declined to comment.

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5. Max de Groen (on behalf of Bain Capital) – Director, Nutanix Inc.
Bain Capital reduced its Nutanix stake by nearly two-thirds over the past year. In June, it sold another 5.5 million shares worth $421 million, reported under board representative Max de Groen. Bain declined to comment.

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6. Michael Rees (on behalf of a Dyal Capital fund) – Co-President, Blue Owl Capital Inc.
Rees oversaw the sale of 20 million Blue Owl shares in May, totaling $395.6 million. The transaction, made through a Dyal Capital fund he leads, was executed in a block trade. Blue Owl did not provide a comment.

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7. Herald Chen – Director, AppLovin Corp.
Chen sold 900,000 AppLovin shares for $340.9 million. Since helping take the company public in 2021, its stock has soared over 300%. Chen, now worth $1.2 billion, stepped down as CFO at the end of 2023 and has begun cashing in on stock options granted when he left KKR & Co. AppLovin did not respond to requests for comment.

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8. Max Viessmann (on behalf of Viessmann Generations Group) – Director, Carrier Global Corp.
Viessmann sold 4.27 million shares worth $300 million in June as part of a portfolio diversification effort. Carrier repurchased the shares in a coordinated transaction. Viessmann remains Carrier’s largest non-institutional shareholder and pledged to continue serving on the board.

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9. Mark Stevens – Director, Nvidia Corp.
Stevens sold over 2 million Nvidia shares, bringing in $288.5 million. He’s filed to sell as many as 4 million shares worth $550 million. A former Sequoia Capital investor, Stevens’ net worth is now $10.8 billion. Nvidia and Stevens declined to comment.

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10. Larry Robbins (on behalf of Glenview Capital) – Director, CVS Health Corp.
Robbins oversaw the sale of 3.75 million CVS shares in May, valued at $253.7 million. The transaction, which reduced Glenview Capital’s stake in CVS by about one-third, aligns with the hedge fund’s strategy to diversify and build capital for new opportunities. CVS remains Glenview’s largest investment.

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