Oracle CEO Tops Jeff Bezos, Dell With $1.8 Billion Stock Sale Last Quarter

Jeff Bezos unloaded hundreds of millions of dollars of Amazon.com Inc. shares last month on his wedding day, but the headline-grabbing transaction wasn’t the largest insider stock sale of the quarter. 

Oracle Corp. Chief Executive Officer Safra Catz exercised and sold stock options worth more than $1.8 billion in the three months ended June 30, surpassing Bezos’ $737 million windfall.

Including the $706 million she disposed of in the first quarter, Catz’s $2.5 billion total makes her the top insider seller of the year so far, according to data from Washington Service, which tracks such buying and selling. It boosted her net worth to $4 billion, according to the Bloomberg Billionaires Index. 

The second quarter started on a turbulent note after President Donald Trump’s April 2 “Liberation Day” tariff announcement spawned an early downturn. Pauses in the tariff proposals, along with renewed interest in the tech sector, pushed the stock market back to new highs by the end of June, when Catz unloaded her shares as part of a predetermined trading plan.

Even with the market rebound, insider selling was down from the same period a year ago. Roughly 6,000 insiders sold about $36 billion of shares in the most recent quarter, compared with almost 9,000 insiders selling $62 billion in the second quarter of 2024, according to Washington Service data.

Only Catz and Dell Technologies Inc. CEO Michael Dell sold shares worth more than $1 billion in the period. Still, more sales are expected from Bezos, who filed a plan to dispose of 25 million Amazon shares worth around $5 billion by next May and has continued selling in July. 

Here are the top insider sellers during the second quarter, according to Washington Service. The data include board directors who report insider sales on behalf of their firms:

1.  Safra Catz

CEO, Oracle Corp.

Total shares sold: 8,694,918

Total value sold: $1,825,887,891

Catz unloaded a total of 8.7 million shares in the quarter, pulling down more than $1.8 billion. Thanks to a performance plan, she received 5 million new options in June, which she exercised and sold along with existing options that were set to expire this month. She regularly receives and exercises stock options, while maintaining a small holding of 1.1 million Oracle shares. A representative for Austin-based Oracle didn’t respond to a request for comment.

2.  Michael Dell

CEO, Dell Technologies Inc. 

Total shares sold: 10,000,000

Total value sold: $1,222,700,000 

Dell sold 10 million shares in the three-month period, a familiar pattern for the founder of his eponymous computer company. After selling two blocks of 10 million shares in the fall, garnering $2.3 billion, he netted an additional $1.2 billion after offloading another chunk at the end of June. The CEO is now the 11th-richest person in the world with a net worth of $136.9 billion, according to Bloomberg’s wealth index. The Round Rock, Texas-based company rejoined the S&P 500 Index in September after a decade-long absence and has seen a surge in revenue tied to its artificial intelligence server business. A spokesperson for Dell Technologies didn’t respond to a request for comment.

3. Jeff Bezos

Chair, Amazon.com Inc.

Total shares sold: 3,324,926 

Total value sold: $736,683,388 

Bezos’ sale of 3.3 million Amazon shares coincided with his wedding festivities, netting him $736.7 million. The world’s fourth-richest person with a $245.5 billion fortune, Bezos adopted a 10b5-1 trading plan in March to sell up to 25 million shares worth roughly $5 billion by next May. The June sales were his first of the year, although he’s gifted nearly 930,000 shares to nonprofits in 2025 as well. Since 2002, Bezos has unloaded Amazon stock worth about $45 billion, but has purchased only a single share, according to data compiled by Bloomberg. A spokesperson for Seattle-based Amazon didn’t respond to a request for comment.

4. David Baszucki 

Chair & CEO, Roblox Corp. 

Total shares sold: 7,420,147 

Total value sold: $630,900,513

Roblox’s smash hit Grow A Garden  video game helped its stock price nearly double in the second quarter, with Baszucki cashing in on the success.  Since April, the CEO has sold more than 7.4 million shares held in a combination of trusts and his family foundation. The sales, which were executed under a 10b5-1 plan adopted in November 2024, netted Baszucki more than $630 million, pushing his net worth to $6 billion, according to Bloomberg’s wealth index.  A representative for the San Mateo, California-based gaming platform didn’t respond to a request for comment.

5. Max de Groen (on behalf of Bain Capital) 

Director, Nutanix Inc.

Total shares sold: 5,480,467

Total value sold: $420,954,670

De Groen serves on the board of Nutanix as a representative for Bain Capital, which has reduced its stake in the cloud-computing company by two-thirds over the past year. Last summer, Boston-based Bain converted a note and received 16.9 million shares. At the time, de Groen said the firm had no plans to sell, but in March it unloaded a third of its position. In June, Bain sold another 5.5 million shares, which are reported under de Groen’s name. A spokesperson for Bain declined to comment.

6. Michael Rees (on behalf of a Dyal Capital fund)

Co-president, Blue Owl Capital Inc.

Total shares sold: 20,000,000 

Total value sold: $395,600,000 

Rees created Blue Owl Capital in 2021 after merging his Dyal Capital Partners with another firm. In May, one of Dyal Capital’s funds converted and then sold shares of Blue Owl in a trading block for nearly $400 million. The transaction is reported under Rees as the firm’s co-president and principal investor in the fund. A spokesperson for New York-based Blue Owl declined to comment.

7. Herald Chen

Director, AppLovin Corp. 

Total shares sold: 900,000

Total value sold: $340,890,648 

Chen joined AppLovin in 2019 as chief financial officer and took the company public two years later. It has seen explosive growth since then with it stock price climbing more than 300% since its market debut. The jump has made several AppLovin executives billionaires, including Chen, whose net worth is $1.2 billion, according to the Bloomberg Billionaires Index, which is valuing his fortune for the first time. Chen stepped down as CFO at the end of 2023 and only recently started selling the stock options he received after being recruited away from KKR & Co. Representatives for Palo Alto, California-based AppLovin didn’t respond to a request for comment.

8. Max Viessmann (on behalf of Viessmann Generations Group)

Director, Carrier Global Corp. 

Total shares sold: 4,267,425 

Total value sold: $299,999,978 

Viessmann is the son of billionaire Martin Viessmann and the fourth generation of his family to run the German heating and cooling business. In 2024, Carrier Global completed its acquisition of Viessmann Climate Solutions, the largest division of the family’s business, and Viessmann joined the board. He sold a portion of his holdings in June 2025 to “support portfolio rebalancing” and Carrier Global repurchased the same amount, resulting in $600 million in proceeds. “I am selling a small percentage of my shares for typical diversification reasons, but I remain the largest non-institutional shareholder and currently aim both to keep it that way and to continue serving on Carrier’s board for years to come,” Viessmann said in a statement at the time.

9. Mark Stevens

Director, Nvidia Corp. 

Total shares sold: 2,027,933 

Total value sold: $288,479,263 

Stevens sold more than 2 million shares of Nvidia in June, but could soon be unloading more. In an SEC filing last month, he proposed selling as many as 4 million shares worth around $550 million. The former Sequoia Capital investor has so far disposed of about half that amount, netting him almost $290 million. He’s currently worth $10.8 billion, according to Bloomberg’s wealth index. Stevens and a spokesperson for Santa Clara, California-based Nvidia declined to comment. 

10. Larry Robbins (on behalf of Glenview Capital)

Director, CVS Health Corp. 

Total shares sold: 3,750,000 

Total value sold: $253,695,413 

Glenview Capital Management pared its stake in CVS by about a third in May, selling 3.75 million shares worth about $250 million. Robbins, Glenview’s founder and CEO, joined the board of CVS last fall as part of an agreement with the activist investing firm. Despite the stock sales, which are reported under Robbins’ name, the health-care company remains the hedge fund’s largest investment, Glenview said at the time. The share sales were “consistent with our fund’s diversification parameters and to create buying power for further unique opportunities in this volatile macro environment,” according to the statement.