Enron Short Seller Jim Chanos Closes Out Bet Against Saylor’s Strategy After 50% Drop

Famous short seller Jim Chanos has officially cashed out his trade against Michael Saylor’s bitcoin empire… and, in true Chanos fashion, he left the table with profits in hand and a familiar grin.

After months of taunting from crypto diehards and Saylor himself, Chanos said he’s unwound his pair trade (shorting Strategy while going long bitcoin) because the gap between the company’s share price and the actual value of its bitcoin stash has all but vanished.

And that’s exactly what happened. Strategy’s stock has cratered nearly 50% from its 2025 peak, while bitcoin itself is still hovering near record highs. That effectively erased the hefty “Saylor premium” investors once paid for owning shares of his leveraged bitcoin holding company.

When Chanos first laid out this trade at his Bears in Hibernation Conference last December, the math was wild… Strategy’s market cap was 2.5x its bitcoin holdings. In simple terms, investors were shelling out $2.50 for every $1 of bitcoin the company actually owned. Fast forward to now, and that number’s collapsed to around 1.2x. “While there’s probably still a little air left to leak, the thesis has largely played out,” Chanos said on X, where he declared victory.

Depending on when he entered and exited, analysts estimate Chanos may have pocketed gains of up to 50% on the trade… a solid payday for a man who once called out Enron before it imploded.

Meanwhile, Strategy founder Michael Saylor, one of Bitcoin’s biggest advocates, has spent years taking on debt and selling stock to buy more crypto… a plan that soared in bull markets but now looks more fragile as prices waver.

Earlier this year, Saylor brushed off Chanos’s criticism, saying he “didn’t understand the business model.” Chanos’s rebuttal? “Financial gibberish.”

The market seems to agree. Investors have grown less eager to pay a markup for Saylor’s financial engineering, especially as other firms rush to copy his bitcoin-holding playbook. Add in a 20% October dip in bitcoin and a new rally in gold, and suddenly Strategy’s cult-like allure has dimmed.

Chanos isn’t betting on a total collapse, but he believes the stock’s valuation will keep falling until it matches the true value of its bitcoin reserves. For the famed short seller, that’s mission accomplished.

At the time of publishing this article, Stocks.News holds positions in Bitcoin and Ethereum as mentioned in the article.