Famed short-seller James Chanos believes that business intelligence firm Strategy is one of the greatest pure arbitrage opportunities he has ever seen.
Chanos argued that there is an "$80B actionable spread" between Strategy and the Bitcoin it holds.
Strategy owns an enormous amount of Bitcoin, but the stock market can value the company at substantially less than the market value of those Bitcoin holdings.
Strategy currently holds about 847,363 BTC. With Bitcoin around $64,000 on August 18, those holdings are worth approximately $54 billion.
That said, MSTR and Bitcoin are not economically identical. Owning MSTR gives you exposure to Bitcoin, but also exposure to Strategy's debt, preferred securities, financing costs, software business, and management decisions.
Chanos's bet against Saylor
Chanos is a famous short seller, and he previously argued that MSTR was trading at an enormous premium to its Bitcoin holdings. In 2025, he explicitly described his trade as selling MSTR while buying Bitcoin.
Chanos and his firm, Chanos & Co., began building the position in late 2024, with reporting placing the initial short around October-November 2024. By November, MSTR’s multiple to the value of its Bitcoin holdings had risen above 3x at points.
From late 2024 into 2025, MSTR's premium over its underlying Bitcoin exposure contracted dramatically. By November 2025, the mNAV had fallen to roughly 1.23x.
Chanos exited the trade in November 2025. More precisely, Chanos & Co. unwound the MSTR/Bitcoin hedge on Nov. 7.
The short-seller's most famous trade was Enron. Chanos began investigating the company in 2000 after noticing that aspects of its financial statements did not make economic sense.
In 2020, Chanos shorted Luckin Coffee. Luckin subsequently disclosed that roughly $310 million in 2019 sales had been fabricated.
The Wirecard trade was another major success. Chanos became convinced that the German payments company was not nearly as profitable as it claimed.
