Short Seller Jimmy Chanos Bets Against MicroStrategy—While Quietly Stacking Bitcoin

Famed bear Jim Chanos takes a chainsaw to MicroStrategy’s stock, calling it ’overpriced hype’—even as his firm accumulates BTC. The ultimate hedge play, or just Wall Street theater?

MicroStrategy’s relentless Bitcoin buying spree now faces its loudest critic. Chanos—who made his name shorting Enron—sees MSTR as a bloated proxy for crypto mania. But his simultaneous Bitcoin buys reveal a deeper game.

One rule still holds: When short sellers talk their book, check their other pockets first. Especially in a market where ’fundamentals’ just means which whale has the heavier bag.

Jim Chanos says Strategy misleads retail investors

Jimmy also called out how MicroStrategy and other companies are selling the idea of holding crypto inside a corporate body. He said they are basically telling retail investors that they should assign a high valuation to these companies just because they hold Bitcoin.

“If you look at where MicroStrategy and now, more ominously, some of its copycat companies that are now raising lots of money are doing is they are basically selling retail investors the idea that we are going to buy bitcoin in a corporate structure. Because of what MicroStrategy has done, you should value us at a similar premium,” Jimmy said. He called that idea “ridiculous.”

Instead of buying into that pitch, Jim said he’s taking the other side. He’s shorting MicroStrategy stock while buying Bitcoin itself. “We’re doing exactly what MicroStrategy and Michael Saylor are doing,” he said. “We’re selling MicroStrategy stock and buying bitcoin and basically buying something for $1, selling it for two and a half dollars.”

Jimmy believes this setup works in his favor because it exposes the disconnect between the company’s market price and the value of what it owns. And the numbers back that up. 

Strategy stock has jumped more than 220% over the last year, while Bitcoin only went up 70% in that same period. That’s why Jim said his trade is a “good barometer of not only just of the arbitrage itself, but I think of retail speculation.”

He didn’t talk much about President TRUMP during the interview, but the crypto rally since early April has been mainly tied to the President’s tariff announcement. Trump has shown public support for crypto during this period, and prices have followed the tone from his administration.

At least for a few months anyway, since as Cryptopolitan reported this morning, the market has actually stopped caring about Trump after he pulled one too many insider trading tricks.

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