- Jim Chanos completed a profitable short position against Michael Saylor‘s Strategy (formerly MicroStrategy) in November 2025.
- He implemented a pair trade: shorting MSTR stock while going long on Bitcoin (BTC).
- Chanos earned about 100% on the short position and gained an additional 25% from Bitcoin Price increase.
- Strategy holds roughly $66 billion in bitcoin but trades at a 1.27x multiple-to-net asset value (mNAV), which fell significantly during Chanos’s trade.
- Chanos’s trade mimicked Saylor’s own approach by selling MSTR shares to buy BTC, profiting from the decline in MSTR premium versus bitcoin.
In November 2024, Wall Street investor Jim Chanos initiated a trade against Michael Saylor’s company, Strategy (previously MicroStrategy), by short-selling its common stock while simultaneously buying bitcoin (BTC). He closed this position in November 2025, likely doubling his money through the short sale and additional BTC gains.
At the time of Chanos’s entry, Strategy had an enterprise value of $84 million and owned about $66 billion in bitcoin. The company traded at a 1.27x multiple-to-net asset value (mNAV), a metric comparing market value to underlying asset worth. However, this premium drastically shrank from an initial 3x in November 2024 to 1.23x when Chanos fully exited.
Chanos publicly shared his thesis on social media and at his annual conference in December 2024, highlighting the mNAV’s decline from 3x to approximately 2.5x as the trade progressed. Over this timeframe, bitcoin’s price rose roughly 25%, boosting profits on the long BTC leg of the trade. His two-legged approach allowed him to profit both from a falling premium on MSTR and a rising bitcoin price.
On multiple occasions, Chanos described his strategy as selling MSTR shares to purchase bitcoin, mirroring Saylor’s own leverage-driven acquisition method. He termed Saylor’s description of buying BTC on leverage as “ridiculous” and “financial gibberish.” He noted that Strategy’s frequent sales of MSTR stock to raise capital were key catalysts for the trade.
The trade earned strong reactions from supporters of Saylor and the “Irresponsibly Long MSTR” community, but public confirmation came through Chanos’s social media, where his victory message gained over one million impressions.
More information about this trade can be found in the original announcement and on CNBC coverage.
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