Veteran short-seller Jim Chanos, historically known for his skepticism toward crypto, has taken a surprising new position that both challenges his past views and leverages market inefficiencies.
Speaking at the Sohn Investment Conference in New York and in an interview with CNBC, Chanos revealed that he is shorting shares of Strategy Inc. (formerly MicroStrategy) while simultaneously going long on Bitcoin.
He likened the move to “selling something for $2.50 and buying it back for $1,” arguing that a major pricing disconnect has emerged between Bitcoin itself and the companies holding large reserves of the asset.
Strategy’s Premium Doesn’t Justify the Valuation, Says Chanos
Chanos argues that Strategy’s stock is overvalued simply because of its massive Bitcoin holdings, with the company enjoying a premium that he considers unjustified.
“It’s absurd,” Chanos said, framing the position as both an arbitrage opportunity and a critique of retail investor behavior, which he believes has pushed Strategy’s stock beyond its fundamental value.
Strategy, under the leadership of Michael Saylor, is the largest publicly traded corporate holder of Bitcoin, with roughly 568,840 BTC worth around $59 billion as of May 2025.
The firm’s aggressive Bitcoin accumulation strategy, initiated in 2020, has caused its stock to soar more than 1,500%, vastly outperforming broader market indices.
Chanos, however, remains unconvinced by the hype. He sees buying Bitcoin directly as a far more efficient approach for investors than gaining exposure through overvalued equities like Strategy.
Chanos Challenges the Strategy Bull Case
His view diverges sharply from that of Strategy insiders, such as analyst Jeff Walton, who recently appeared in a Financial Times documentary suggesting that Strategy could one day become the world’s most valuable public company.
Walton’s optimism hinges on Strategy’s extensive Bitcoin exposure and the belief that BTC is “the most pristine collateral on the planet.”
But for Chanos, the retail enthusiasm surrounding crypto-heavy stocks is reminiscent of past speculative bubbles. He believes investors are overpaying for the convenience of indirect crypto exposure via public equities.
From Bitcoin Skeptic to Direct Holder
Chanos has been one of Bitcoin’s loudest critics for years. In 2018, he dismissed the asset as a “libertarian fantasy” and claimed that in a real crisis, tangible assets like food would hold more value than digital currencies.
He has also previously condemned crypto’s role in facilitating illicit financial transactions, once labeling the industry as “the dark side of finance.”
However, Chanos now views owning BTC directly as a more rational play than holding crypto through inflated stocks or ETFs. He recently criticized the rise of spot Bitcoin ETFs, suggesting they are more about fee extraction than belief in blockchain innovation.
A Legendary Short Seller Eyes Arbitrage Again
Chanos gained fame for correctly shorting Enron before its infamous collapse in 2001, reaping massive returns for his firm, Kynikos Associates. But not all his calls were successful—most notably, his long-standing short of Tesla, which led to significant losses and ultimately the transformation of Kynikos into a family office.
Now, with Bitcoin crossing the $104,000 mark, the debate between Strategy bulls like Walton and skeptics like Chanos is intensifying.
While Walton believes Strategy’s BTC-focused approach gives it an unparalleled edge in the market, Chanos argues the company is riding a speculative premium that could unwind if sentiment shifts.
For now, Chanos is betting that the value lies not in the hype of crypto-linked stocks—but in Bitcoin itself.
