Like it or not, Jim Chanos’ MSTR short trade was a winner

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Headline, Like it or not, Jim Chanos' MSTR short trade was a winner. Published at 1218 PM, August 27, 2025 Although they'd hate to admit it, even Michael Saylor's biggest fans would agree that Jim Chanos' bearish strategy, MSTR, trade this year, has been exceptionally profitable. Chanos sold shares short and fully hedged that short sale with a long Bitcoin BTC position. In other words, rather than betting against MSTR's overvaluation on an absolute basis, he merely prepared for its premium relative to its BTC holdings to collapse. It has. On May 14, at the 2025 New York Sone Investment Conference, Chanos explained that he'd been building his short position in strategy, formerly microstrategy, since its 2.5 XMN-AV in November 2024 On numerous podcasts and interviews over the past few months, he's reiterated that his overall cost basis is above 2 XMN-AV. That's a terrific cost basis for someone betting a low single-digit percentage of his fund on the price of MSTR declining. As of today, MSTR's basic MN-AV has declined to 1.4 2X, and its newly introduced enterprise value MN-AV is 163X.

The acronym MN-AV refers to the multiple of strategies market capitalization to its colloquial net asset value, NAV. Even though companies don't have a NAV, technically speaking, crypto investors colloquially refer to a company's crypto holdings as its NAV. Strategies NAV is approximately $70 billion. Needless to say, Chanos' trade has been very profitable. Any shares he sold short, at 2.5 XMN-AV, are worth at least 34% more today, below 164X. For a fund manager benchmarking to the returns of the S&P 500 index since November 1st, 2024, that 34% gain outperforms his benchmark by an impressive 2,100 basis points. Even shares sold short, at 2 XMN-AV have outperformed the S&P by at least 500 basis points. Buying something for $1, selling it for $2.50. Of course, Chanos' two-pronged trade involves margin costs and management fees, so he's paid out some of those basis points to execute his strategy. Overall, and depending on the assumptions you make about his cost basis and fees, Jim Chanos' hedged MSTR short sale position is probably up 15 to 35% versus the S&P's 13% gain since November 1st, 2024 This range assumes that Chanos didn't avail himself of margin to multiply his position on leverage. Read more. Michael Saylor says Bitcoin credit now has a yield curve. Thanks to him. On the day of the SONE NYC conference, Chanos told CNBC News, we are selling micro-strategy stock and buying BTC, and basically buying something for $1, selling it for $2.50.

In addition to his gains from his hedged short sale, Chanos has also succeeded at advertising himself and his fund through his bearish media tour. Continuing his career as a skeptical short seller and risking less than 10% of his fund on the actual trade, Chanos has appeared on numerous podcasts and video interviews about his bet against Sailor's BTC Treasury Company. In all, Chanos has succeeded alongside Sailor himself. Like Sailor, he buys BTC and sells MSTR. The main difference between the pair is their long-term plan. Whereas Sailor plans to buy BTC and sell MSTR forever, Chanos plans to eventually cover his short and sell BTC to close that hedge. This recording is AI-generated. Get more crypto news at protos.com.