Careful MSFT, AMZN, ORCL Bulls: Trouble at OpenAI, Anthropic Could Trigger 'Sustained' AI Selloff, 'Big Short' Legend Says

Steve Eisman, the investor made famous by “The Big Short,” says the next leg down in the AI trade may start with two companies that aren’t publicly traded.

In an episode of The Weekly Wrap released Friday, Eisman named the health of OpenAI and Anthropic as “a key thing to monitor to determine a catalyst for a real sustained selloff.” “The entire AI ecosystem could go through a correction phase because so much of the hyperscaler backlogs are from these two companies,” he said.

Why the Backlogs Are the Pressure Point Eisman has argued before that the big model labs lack moats, a vulnerability he said could intensify if cheaper Chinese open-source models force a price war.

His warning is now sharper.

Hyperscalers such as Microsoft (NASDAQ: MSFT ), Amazon (NASDAQ: AMZN ) and Oracle (NYSE: ORCL ) have real, fast-growing cloud businesses, but Eisman argues that much of the sector’s order book ultimately depends on the model labs.

Oracle most recently reported $638 billion in remaining performance obligations, and Eisman estimated roughly half is tied to OpenAI.

He cautioned that anyone confident about AI’s endgame is “kidding themselves” because the facts change weekly.

Credit Markets Begin to Worry The concern is already visible in debt markets.

CoreWeave (NASDAQ: CRWV ) is raising a $2.6 billion loan to fund computing capacity for customers including Anthropic, with the debt priced to yield above 9%.

That is far more than investment-grade giants such as Alphabet pay to borrow, a premium that signals lenders see greater risk in debt supported by CoreWeave’s Anthropic contracts. “That is expensive debt,” Eisman said. “There is something of a credit cycle here,” with investors now distinguishing between cash-rich hyperscalers that can clearly repay and smaller, newer borrowers whose fortunes ride on a handful of AI customers.

Polymarket’s AI bubble burst in 2026 market is currently at 19%.

It rose as high as 27% last week.

The high came as Situational Awareness, Leopold Aschenbrenner ‘s fund that reportedly grew to as much as $45 billion, sold much of its stock portfolio to Citadel after margin calls.

Eisman said the funds collapse shows there is more to running a hedge fund than being smart. “Risk management is key,” he said. “Making money on the upside is great, but protecting the downside is just as important, maybe even more so.” Image: Shutterstock Read Also: Ray Dalio Says US Is in Decline: 'Threats No Longer Work' in a World Where Order Breaks Down