New York, April 28, 2026, 08:01 EDT
Oracle shares tumbled 7.7% to $159.80 in premarket action Tuesday, after the Wall Street Journal said OpenAI has been missing user and revenue milestones—shaking up firms linked to the ChatGPT developer. CoreWeave slipped 7.4%. In Tokyo, SoftBank ended the session down nearly 10%, according to Reuters.
This shift is significant—Oracle’s AI narrative now doubles as a funding play. Reports peg its five-year contract with OpenAI at about $300 billion, an eye-popping figure that puts OpenAI’s future expansion at the heart of how investors size up Oracle’s backlog.
OpenAI failed to hit several monthly revenue goals earlier this year and has ceded ground to Anthropic in both coding and enterprise segments. The company also didn’t meet an internal benchmark for ChatGPT to hit 1 billion weekly active users by late 2025, the Journal said, as cited by Reuters. CEO Sam Altman and CFO Sarah Friar pushed back: “This is ridiculous. We are totally aligned on buying as much compute as we can.” Compute, in this context, refers to the data-center horsepower required to train and run AI models. Reuters
Oracle’s earnings report for March put the spotlight on a closely watched metric. Remaining performance obligations hit $553 billion in the third fiscal quarter—a 325% jump year over year. The company attributed the surge in RPO mainly to big AI deals, pointing out that customers either fronted the cash for hardware or provided their own.
Questions around the balance sheet weren’t new by Tuesday. Last Friday, The Journal highlighted how Oracle’s ambitious OpenAI deal was already stretching banks’ willingness to finance data-center debt. Lenders such as JPMorgan Chase were having a tough time offloading risk from loans linked to Oracle’s leased facilities in Texas and Wisconsin. Morgan Stanley’s credit team put Oracle’s future cash needs at $100 billion or more for 2027 and the first half of 2028, even after the company secured roughly $50 billion for 2026.
Oracle moved to address the issue in March, announcing plans to secure as much as $50 billion via debt and equity. So far, $30 billion is already in the bag—investment-grade bonds and mandatory convertible preferred stock. The company said it doesn’t plan to issue additional bonds in calendar 2026 above that total.
Pressure hit the OpenAI trade. Just last month, CoreWeave—an AI cloud provider backed by Nvidia—landed an $11.9 billion infrastructure contract with OpenAI. SoftBank, for its part, committed $22.5 billion in funding by year-end, Reuters reported, eyeing cash-raising moves that could include borrowing against its Arm Holdings stake.
The bigger worry isn’t that enthusiasm for AI has dried up. Instead, it’s the speed of spending—pouring money into AI projects before the payback is clear. According to Reuters, Alphabet, Microsoft, Meta, and Amazon are collectively set to shell out some $600 billion on AI this year. Joe Maginot, large-cap portfolio manager at Madison Investments, put it bluntly: “what’s the return on all the capital expenditure?” Capex, or capital expenditure, refers to investments in items like chips, servers, and data centers. Reuters
Monday brought a change in dynamics. Microsoft and OpenAI relaxed their exclusive relationship, opening the door for OpenAI to work with other cloud players, Amazon included. Microsoft still holds on as the main cloud partner—and the company keeps pulling in a 20% revenue share through 2030, though there’s a limit. Gil Luria at D.A. Davidson called the updated Microsoft arrangement “essential for OpenAI to be successful in the enterprise market.” Reuters
Oracle’s sharp drop has some bulls questioning the pace. Dan Ives at Wedbush—he started coverage just last week with an Outperform—calls Oracle a “foundational infrastructure provider” for AI, insisting that what looks like speculation is actually a contract-driven investment cycle. Investors, he says, are misreading it. Barron’s
Before the drop, there was a tactical setup in play. CNBC’s Jim Cramer labeled Oracle’s recent jump as “a short squeeze”—the sort of surge that can trap bearish traders into covering their positions—according to Yahoo Finance and Insider Monkey. Cramer added that Oracle’s ability to push higher depended on cheaper borrowing. But if doubts creep in about those same borrowing assumptions, these rallies tend to unravel quickly. Insider Monkey
The trade’s got sharp edges. OpenAI keeps snapping up compute—great news if Oracle’s customer-funded gear strategy delivers, potentially flipping that backlog into a surge of cloud revenue. But things get tricky fast if OpenAI’s revenue gap lingers or project-finance lenders tap the brakes; suddenly, data-center timelines, funding costs, and Oracle’s AI margin narrative all come under pressure.
