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Oracle Executives Spark Concern with Major Stock Disposals

Robert Sasse by Robert Sasse
October 31, 2025
in Analysis, Insider Trading, Tech & Software
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A wave of insider selling at Oracle has unsettled investors, raising questions about the company’s prospects despite its positioning within the artificial intelligence boom. Senior figures, including a recently promoted co-CEO, have offloaded millions of dollars worth of shares, triggering a sharp market reaction and casting a shadow over the profitability of its cloud division.

Leadership Liquidates Holdings

The selling activity was both substantial and conspicuous. Clay Magouyrk, who was elevated to the role of co-CEO just in September, disposed of 40,000 shares, a transaction valued at approximately $11 million. In a separate move, Director Jeffrey Berg sold 49,361 shares amounting to about $13.9 million through a trust.

This coordinated disposal by top insiders has prompted market observers to ask what these executives might know that the wider investment community has overlooked. The timing is particularly striking given the pervasive optimism surrounding AI-related technologies.

Market Reacts with a Selloff

The financial markets delivered a swift verdict on this insider activity. On Thursday, Oracle shares experienced a steep decline, plunging 6.8% to close near $256. The selloff was accompanied by a dramatic 78% surge in trading volume compared to the daily average, indicating a broad and forceful exit from the stock.

Should investors sell immediately? Or is it worth buying Oracle?

The downturn was severe enough to breach key technical support levels, initiating a negative trend. From its record high reached in September, Oracle’s stock has now fallen more than 25%, marking a significant reversal for a company once celebrated as a definitive AI winner.

Cloud Margin Concerns Come to Light

Analysts were quick to provide a potential explanation for the insider sales. Researchers from the Capital Area Planning Group disclosed they had reduced their own stake in Oracle, citing a critical assessment of the company’s cloud business. Their analysis pointed to cloud margins that are “significantly lower” than those achieved by rivals such as Amazon Web Services and Google Cloud.

Furthermore, they highlighted Oracle’s substantial and potentially risky reliance on a single major client, OpenAI. The very cloud infrastructure powered by Nvidia chips, marketed as a gateway to AI riches, is now being scrutinized as a drain on profitability. Soaring costs for energy and hardware, combined with competitive pricing pressures, are squeezing margins.

All attention now turns to Oracle’s upcoming quarterly earnings report. Investors will be looking for clear evidence of sustainable profitability within its cloud operations. Without such confirmation, the recent selloff could very well continue.

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Robert Sasse

Robert Sasse

About Dr. Robert Sasse Accomplished economist, entrepreneur, and profound expert in financial markets. Dr. Robert Sasse holds a doctorate in economics and combines academic rigor with practical entrepreneurial experience. His deep expertise in economic relationships and unwavering conviction for a free-market liberal economic order drives his mission to provide investors with well-founded knowledge and guidance.
Areas of Expertise:
  • Economic Theory and Practice
  • Free-Market Economics
  • Entrepreneurship and Business Strategy
  • Investment Philosophy
Dr. Sasse's unique combination of academic knowledge and real-world business experience enables him to provide investors with comprehensive insights that bridge theory and practice.

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