Bitcoin Skeptic Jim Chanos Shorts Saylor’s Strategy but Buys BTC

Noted short-seller Jim Chanos, long known for his skepticism toward Bitcoin and crypto markets, has revealed a new trading position that flips his past criticisms on their head.

Speaking at the Sohn Investment Conference in New York, Chanos told CNBC he is now shorting shares of Strategy (formerly MicroStrategy) while simultaneously buying Bitcoin directly.

Describing the trade as “selling something for $2.50 and buying something for $1,” Chanos believes there is a significant mispricing between Bitcoin and the equity of firms holding it.

He argues that companies like Strategy are commanding an outsized market premium simply for holding Bitcoin on their balance sheets.

“It’s ridiculous,” Chanos said, characterizing his trade as both an arbitrage play and a commentary on what he views as excessive retail speculation.

MicroStrategy, now rebranded as Strategy, is led by executive chairman Michael Saylor and is the world’s largest corporate holder of Bitcoin.

As of May 2025, it holds approximately 568,840 BTC, worth an estimated $59 billion.

Since the company began accumulating Bitcoin in 2020, its stock has surged more than 1,500%, far outperforming the broader market.

Chanos believes that exposure to Bitcoin via equities like Strategy is an inefficient and overvalued route for investors.

WATCH: Billionaire Jim Chanos says he's long on #Bitcoin $BTC but short on #MicroStrategy $MSTR, calling it “too leveraged.” pic.twitter.com/NNRSZU2V2N

He argues that retail investors are paying a premium for indirect Bitcoin exposure through public companies, which inflates valuations beyond rational levels.

His position contrasts sharply with Strategy analysts, including Jeff Walton, who recently said in a Financial Times documentary that the firm could become “the number one publicly traded equity in the entire market” due to its BTC holdings.

Chanos has long been critical of Bitcoin and the crypto sector. In 2018, he dismissed Bitcoin as a “libertarian fantasy,” arguing that in a financial collapse, digital assets would have little practical value.

“If the world goes down, I’d rather have food than Bitcoin,” he once quipped. He also criticized the industry for facilitating illicit financial activity, calling crypto “the dark side of finance” in a 2023 interview.

Despite his past criticisms, Chanos now sees direct Bitcoin ownership as a better value than owning crypto-heavy stocks.

He also recently criticized the rise of spot Bitcoin ETFs, suggesting that Wall Street’s interest is driven more by fee generation than by belief in the asset.

Chanos is best known for his legendary short of Enron before its collapse in 2001, which brought massive gains to his firm, Kynikos Associates.

However, not all his bets have been winners. His infamous short of Tesla cost him heavily as the stock soared over 2,000%, leading to his fund’s eventual conversion into a family office.

As reported, Jeff Walton, an analyst at Strategy, has said the firm may one day rise to become the top publicly traded company in the world.

Walton believes the company’s unprecedented exposure to Bitcoin, which recently crossed $104,000, gives it a unique edge.

“Strategy holds more of the best asset and most pristine collateral on the planet than any other company, by multiples,” he said.

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