How Jim Chanos outplayed Michael Saylor: short MSTR, long BTC

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Headline, How Jim Chanos Outplayed Michael Saylor, Short MSTR, Long BTC, Published at 2:07 p.m., November 10, 2025 Wall Street's cynic Jim Chanos has closed out his widely publicized and controversial bet against Michael Saylor's strategy, formerly microstrategy, likely doubling his money through short selling the company's MSTR common stock. To be exact, the short seller constructed a pair trade of short MSTR and long Bitcoin, BTC. Rather than betting that the price of MSTR would decline on an absolute USD basis, Chanos simply bet that the premium of MSTR would decline against BTC strategy is the world's largest digital asset treasury, DOTI Company. A category of publicly traded companies that acquire crypto tokens using financial leverage, rather than focusing on traditional sales of products or services. The company owns approximately $66 billion worth of BTC and trades at an $84 million enterprise value. Market cap plus pro forma net debt, including preferreds. A generous 1.27 times multiple to net asset value, MNAV. Still, that MNAV has declined substantially since Chanos entered his trade. After entering his two-legged position in November 2024, to express doubt that MSTR would outperform BTC, the billionaire Chanos and company founder, closed out his on Friday morning after earning approximately 100 percent. His victory lap on social media earned over 1 million impressions. Short MSTR, long BTC Chanos profited from MSTR's MNAV decline from above three times in November to a likely average around 2.5 times when he shared his thesis at his annual conference in December 2024 By the time he fully closed his trade, its MNAV had declined to 1.23x, a mere 23 percent premium to its BTC holdings. Over the same period, the second leg of his trade had also grown in profit. Since November 2024, the price of BTC has increased roughly 25 percent. In other words, not only did Chanos double his money shorting MSTR, he also earned roughly 25 percent from BTC appreciation, profiting on both legs of his trade. The Family Office Fund Manager has cemented his position as the most successful critic of Saylor. Read more. Saylor to Jim Chanos Three ways your MSTR short is doomed selling MSTR to buy BTC. Just like Saylor Chanos earned immediate vitriol from Saylor fans, like the self-named, irresponsibly long MSTR community, for broadcasting a bearish investment thesis on strategy at the 2025 New York SONE Investment Conference. On numerous televised and social media interviews, Chanos described his bearishness on strategy, maintaining a lofty MNAV. He previously described his strategy as selling micro-strategy stock, and buying BTC, and basically buying something for $1, selling it for $2.50.

He also called Saylor's description of acquiring BTC on leverage ridiculous and financial gibberish. In fact, he characterized his trade as simply replicating the actions of Saylor himself. Selling MSTR to buy BTC Chanos repeatedly noted that Strategy's dilutive sales of MSTR, aggressively selling down its own MNAV to buy BTC, was the trade catalyst that convinced him to initiate his two-pronged trade in the first place. Although Strategy has sold a few billion dollars worth of preferred shares that don't immediately dilute MSTR, it's raised the vast majority of its capital from MSTR sales. Protos reached out to Chanos for comment, but didn't receive a reply prior to publication time. This recording is AI generated. Get more crypto news at protos.com.