The man who made a fortune betting against the housing market before it collapsed in 2008 now has his crosshairs trained on the AI boom. Michael Burry disclosed a fresh batch of short positions on June 30, targeting some of the biggest beneficiaries of the artificial intelligence frenzy.

His targets: Tesla at $416.22, Caterpillar at $1,060.98, Applied Materials at $729.40, Nvidia at $198.09, and the iShares Semiconductor ETF (SOXX) at $642.80. In English: Burry is placing real money on the idea that these stocks are going to fall.

The trades and why they matter

He’s not just going after the obvious AI plays like Nvidia and Applied Materials. He’s shorting Caterpillar, a heavy equipment company that most people associate with construction sites, not data centers.

Caterpillar’s stock surged roughly 86% in the first half of the year, riding an AI-driven market rally that lifted companies far beyond the traditional tech sector. Its price-to-sales ratio has hit a 30-year high, according to Burry’s own analysis shared via his Substack.

The semiconductor sector is flashing similar warning signs. SOXX, the broad semiconductor ETF that Burry is shorting, was trading 65% above its 200-day moving average at the time of his trade.

Tesla, meanwhile, continues to occupy a unique space as both a car company and an AI/robotics play. Burry shorted it at $416.22, suggesting he thinks the stock’s AI premium is, at minimum, overstated.

Burry’s track record and strategy

Burry’s fame rests almost entirely on one legendary trade: his bet against subprime mortgage securities before the 2008 financial crisis, immortalized in Michael Lewis’s book and the subsequent film “The Big Short.”

His recent trades extend a consistent pattern of skepticism toward elevated tech valuations. These June 30 disclosures represent a meaningful expansion of that thesis.

Burry disclosed the trades via his Substack on the same day they were executed. No waiting for quarterly 13F filings. No letting positions build quietly in the background.

What this means for investors

The semiconductor sector deserves particular scrutiny. A 65% premium over the 200-day moving average is historically unusual for SOXX. Past instances of similar overextension have often, though not always, preceded meaningful pullbacks.

A 30-year high in Caterpillar’s price-to-sales ratio doesn’t mean the stock drops tomorrow. It means the margin for error is razor thin, and any disappointment in AI-related spending could trigger a repricing that catches momentum-driven investors off guard.