No matter how good the performance is, the boss cannot withstand selling 50 million shares of Oracle stock. Yesterday, the last part of Oracle's financial report contained a message that kept the stock price falling all the way: Larry Ellison is preparing to sell up to 50 million shares of Oracle stock before October 24th of this year through a pre-set Rule 10b5-1 trading plan. Based on the closing price of approximately $150 on September 11th, the scale is about $7.5 billion; 1. Why is this particularly rare? Ellison has long pursued a "buy, borrow, die" strategy: he hardly sells stocks, but pledges them to banks for loans to avoid triggering capital gains tax. In the future, heirs will also be able to enjoy a cost base increase and a significant reduction in tax burden. In the past 20 years, he has rarely sold more than 25000 shares in a single transaction. Since 2010, the cumulative sales volume has only been about 7.5 billion US dollars, and has never exceeded 1 billion US dollars in a single year. In July 2024, it sold 1.125 million shares, which is a significant move in recent years. This plan may reach the cumulative scale of the past 15 years in one go, indicating that the scale of this sales plan is very large. He currently holds approximately 1.16 billion shares of Oracle, accounting for about 40-41% of the company's total share capital. 277 million to 346 million shares have been pledged as personal loan collateral. 2. Reason for selling: 1) Either helping his son raise funds, Ellison provided over $40 billion in irrevocable personal guarantees for his son David Ellison's media expansion (involving acquisitions of media assets such as Warner Bros. Exploration by Paramount and others). A large number of stocks have been pledged, and after the stock price dropped from a high of $329.50 in September 2025 to around $150 currently, the value of the pledged stocks has significantly decreased, which may require additional liquidity to cover potential liabilities or supplement collateral. 2) Either they are getting older and need to engage in diversified asset allocation. 50 million shares account for about 1.7% of the company's outstanding shares (with a total share capital of approximately 2.88 billion shares), which is actually a considerable amount. In the short term, it will definitely create pressure on stock prices. And in the first fiscal quarter ending on August 31, 2026, Oracle has just completed a $20 billion ATM stock financing. The company just sold out its stocks, and then the boss came to sell again.