- Jim Chanos profited significantly in 2025 by shorting Strategy (MSTR) shares while holding a long position in Bitcoin (BTC).
- Chanos began building his short position when MSTR traded at 2.5 times its net asset value (mNAV) in November 2024.
- By May 2025, the premium of MSTR’s market value over its bitcoin holdings dropped sharply, enhancing returns for the trade.
- Chanos stated he was “selling MicroStrategy stock and buying BTC,” capturing value from the gap between share price and asset backing.
- The strategy outperformed the S&P 500 by 500–2,100 basis points, depending on entry point and fees.
Jim Chanos executed a profitable investment strategy in 2025 by shorting shares of Strategy (formerly MicroStrategy) and hedging the position with a simultaneous long holding in bitcoin. This approach aimed to exploit the difference between the company’s share price and the value of its bitcoin assets.
Chanos began building his short position at the 2.5x mNAV level in November 2024, according to comments made at the 2025 New York Sohn Investment Conference. The mNAV, or multiple of market capitalization to net asset value, is calculated using the sum value of bitcoin held by the company. As of May 2025, Strategy’s mNAV had dropped to 1.42x, with a newly introduced enterprise value mNAV at 1.63x. Strategy’s estimated bitcoin holdings have a net asset value of approximately $70 billion.
On the day of the Sohn NYC conference, Chanos shared his method with CNBC News, stating, “We’re selling MicroStrategy stock and buying BTC and basically buying something for $1 selling it for $2.50.” Any shares shorted at 2.5x mNAV were at least 34% more valuable when covered at prices below 1.64x, translating to gains that surpassed the S&P 500 by as much as 2,100 basis points for those early trades. Even later short positions at 2x mNAV outperformed the S&P by a minimum of 500 basis points.
Chanos explained on multiple podcasts and interviews that his overall cost basis was above 2x mNAV. His hedge strategy meant he was not betting against bitcoin itself, but rather against the premium investors placed on MSTR relative to its crypto holdings. Execution of this hedge incurred management fees and margin costs, but, depending on these factors and the size of his positions, Chanos’s strategy was up an estimated 15%–35% compared to the S&P 500’s 13% gain over the same period.
While both Michael Saylor, Strategy’s chairman, and Jim Chanos were buying bitcoin and selling MSTR during this period, Chanos planned to cover his short position and unwind the hedge eventually, unlike Saylor’s longer-term approach. Chanos publicized his trade widely, appearing on sources such as CNBC to discuss the details.
The acronym mNAV refers to the commonly used crypto investor calculation that compares a company’s market value to its net assets, in this case, primarily its bitcoin holdings. Companies do not officially have a NAV, but in the context of crypto-heavy firms like Strategy, this metric is used to gauge whether shares trade at a fair value relative to underlying assets. As of May 2025, Strategy’s NAV is calculated at roughly $70 billion.
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