Oracle executives sold millions in stock after a strong AI-fueled rally. The moves raised questions about whether the company’s rapid climb can keep going.

Oracle has been a standout of the AI build-out, and senior leaders are taking some profits. On Oct. 21, newly appointed co-CEO Clay Magouyrk sold 40,000 shares at an average of $276.64 for proceeds of roughly $11 million. He still directly owns 154,030 shares, worth about $43.6 million at Friday’s close of $283.33. Moreover, the sales came after a blistering September in which Oracle shares jumped 24 percent, easily topping the S&P 500’s 3.5 percent gain.
Chief accounting officer Maria Smith also trimmed exposure. She sold 5,000 shares at $280 on Oct. 21 and another 5,000 shares around $280.62 on Thursday, for total proceeds of about $2.8 million. After these sales, Smith directly owns 47,083 shares, a stake valued near $13.3 million at Friday’s close. In addition, director Jeffrey Berg filed a Form 144 indicating an intent to sell 43,365 shares on Oct. 28, signaling more insider activity ahead.
Investors can track these sales and their details on TipRanks Insider Trading Tool. Click on the image below to find out more.

Regulatory filings indicate Magouyrk and Smith sold restricted stock that had previously vested. Restricted stock units convert into shares or cash once service or performance conditions are met, so these disposals often reflect planned diversification rather than a fundamental call on the business. Even so, investors tend to scrutinize the timing when sales land after a sharp rally.
Oracle’s rally has been steep. The stock is up more than 70% this year, while the S&P 500 (SPX) has risen about 15 percent. As prices rise, executives frequently rebalance concentrated positions. Furthermore, the company’s leadership still holds sizable stakes, which helps align incentives even as they take some chips off the table.
The core debate is straightforward. Oracle’s AI and cloud story keeps building, yet insider sales can unsettle sentiment at the margins. In recent quarters, Oracle has doubled down on cloud infrastructure and high-performance computing to capture more of the booming AI market. As a result, the company now finds itself competing directly with Microsoft (MSFT) and Amazon (AMZN) for major contracts. At the same time, rising demand for large-scale model training has turned Oracle’s expanding network of data centers into a central driver of growth.
Short term, insider selling can act as a speed bump. Longer term, institutional holders will look through one-off transactions and focus on bookings, backlog, and margins from AI-driven demand. If growth in cloud services and AI server rentals stays firm, the stock’s trajectory will likely track fundamentals rather than Form 4 headlines.
Oracle’s shift to cloud has expanded its total addressable market and strengthened recurring revenue. In addition, the company keeps landing AI-focused projects that demand powerful computing and fast networking. These wins are helping drive stronger revenue growth and could boost profitability over time.
Investors should keep an eye on customer wins, utilization, and cash flow. Insider sales may draw attention for a moment, but consistent performance in cloud and AI is what ultimately drives Oracle’s valuation.
Turning to TipRanks, it seems that Oracle stock still has room to run, according to Wall Street analysts.
Based on 36 recent ratings, the stock carries a “Moderate Buy” consensus, with 25 Buys, 10 Holds, and one Sell.
The average 12-month ORCL price target sits at $354.13, implying a 24.99% upside from the latest close.

