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

Wall Street 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 (DAT) 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 1.27x 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 & Co. founder closed out his on Friday morning after earning approximately 100%.

His victory lap on social media earned over 1 million impressions.

Short MSTR, long BTC

Chanos profited from MSTR’s mNAV decline from above 3x in November to a likely average around 2.5x 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% 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%.

In other words, not only did Chanos double his money shorting MSTR, he also earned roughly 25% 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.

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 Sohn 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 MicroStrategy 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.

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