AI Bet Backfires? Oracle Stock Suffers Worst Week in 25 Years as Financing Fears Mount

Oracle’s stock experienced its sharpest weekly decline since 2001, plummeting 19% amidst mounting investor concerns over its massive debt load and aggressive investments in AI infrastructure. The company’s capital expenditures surged, leading to significant negative free cash flow, as it races to compete with cloud giants. Despite widespread analyst optimism, the software firm faces balance sheet risks and market headwinds, impacting co-founder Larry Ellison’s personal wealth ranking.

Key Points

Oracle's stock plummeted 19% this week, marking its steepest decline since August 2001, the heart of the dot-com bust.
The company's capital expenditures soared by 162% in the latest fiscal year, resulting in nearly $24 billion in negative free cash flow and a staggering $130 billion in debt.
Co-founder Larry Ellison has seen his position on the world's richest list slip behind tech luminaries like Google's co-founders, Amazon's Jeff Bezos, and Michael Dell.

AI Bet Backfires? Oracle Stock Suffers Worst Week in 25 Years as Financing Fears Mount — Oracle CEO Clay Magouyrk, right, speaks on a media tour of the Stargate data center in Abilene, Texas, on Sept. 23, 2025. *Credit: Kyle Grillot | Bloomberg | Getty Images*

The company's shares plunged 19% over the week, experiencing drops of at least 2.6% each trading day. This downturn represents the most significant weekly retreat since a 20% freefall in August 2001, amidst the fallout from the dot-com bubble.

Oracle investors have faced a harsh nine-month period. After achieving a peak market capitalization of $900 billion last September, fueled by optimism surrounding its AI clientele, the stock has since shed approximately 55% of its value. The core issue stems from Oracle's strategy to fulfill its substantial AI infrastructure commitments, notably to OpenAI, which necessitates acquiring record levels of debt. This strategy introduces considerable balance sheet risk while focusing on offerings with potentially lower profit margins.

As of the end of May, Oracle carried about $130 billion in debt, with capital expenditures escalating by 162% to nearly $56 billion in the fiscal year 2026. The company is in a fierce race to establish new data centers, directly competing with cloud titans like Amazon, Microsoft, and Google, yet it lacks the ability to offer a comprehensive technology stack akin to its rivals.

Oracle reported a negative free cash flow of almost $24 billion in its latest fiscal year. Earlier this month, the company announced intentions to secure $40 billion through debt and equity financing in fiscal 2027, including a $20 billion share sale, building on $43 billion in debt sales and $5 billion from equity issuance in the prior fiscal year.

"We expect financing/leverage and the pace of equity issuance to remain the central investor debate near term, even as demand signals stay strong," Evercore analysts, who maintain a 'buy' rating on the stock, commented in a recent note.

Despite mounting investor anxiety, many firms, including Evercore, remain optimistic about Oracle's future. FactSet data shows that 71% of analysts recommend purchasing Oracle stock, the highest percentage in 15 years.

Oracle did not provide a comment when requested.

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Oracle is navigating multiple market challenges. In addition to its substantial capital requirements, the company's stock has been affected by a broader selloff in software sector, driven by investor worries that advanced AI models might render many of their products obsolete. The iShares Expanded Tech-Software Sector Exchange-Traded Fund (IGV) has fallen 16% thus far in 2026, while Oracle's shares have dropped 24%.

In its recent annual report, Oracle disclosed a 13% reduction in headcount, bringing its total to 141,000 employees in fiscal 2026, with a noticeable decrease in sales and marketing roles.

Larry Ellison, Oracle's co-founder, was conspicuously absent from this month's earnings call, leaving co-CEOs Clay Magouyrk and Mike Sicilia, along with recently appointed finance chief Hilary Maxson, to address investor inquiries.

"Hilary has a tough life," Magouyrk remarked during the call.

The decline in Oracle's stock price has caused Ellison's net worth to fall, placing him behind Google co-founders Larry Page and Sergey Brin, Amazon's Jeff Bezos, and Michael Dell on the global list of wealthiest individuals. Despite this, Ellison's fortune still exceeds $200 billion.

Oracle remains committed to its expansion plans, targeting new data centers in Michigan, New Mexico, and Texas for 2027.

"As we pursue these opportunities, we'll remain focused on disciplined capital allocation, maintaining a strong balance sheet, and preserving our investment-grade credit rating," Maxson stated during the earnings call this month.