Investor Jim Chanos announced a short position on Strategy (MSTR) stock while going long on Bitcoin, citing the company’s significant premium relative to its Bitcoin holdings.
With 177% gains over the past year and 40% since the start of 2025, investor Jim Chanos believes that this is the right time to short Strategy (MSTR) stock. Previously dubbed MicroStrategy, the MSTR stock has enjoyed a premium over Bitcoin BTC $114 236 24h volatility: 2.1% Market cap: $2.28 T Vol. 24h: $59.75 B gains for a long time, amid its aggressive Bitcoin acquisition strategy.
While speaking on the sidelines of the Sohn Investment Conference in New York, investor Jim Chanos revealed his short position on MSTR. However, he disclosed that he’s simultaneously going long on Bitcoin. In an interview with CNBC, Chanos said:
“We’re selling MicroStrategy stock and buying Bitcoin and basically buying something for $1 selling it for two and a half dollars.”
Strategy’s Big Bitcoin Bet and MSTR Stock Surge
For years, Strategy’s MSTR stock has been a big proxy bet on Bitcoin, especially for institutional players who did not have access to the asset. With its aggressive Bitcoin purchases, the company has still managed to maintain that additional alpha on Bitcoin returns.
However, MicroStrategy has used leverage to build its Bitcoin reserves and currently trades at a significant premium relative to the value of its Bitcoin holdings. Warning about it, investor Chanos said:
“If you look at where MicroStrategy and now, more ominously, some of its copycat companies that are now raising lots of money are doing, they are basically selling retail investors the idea that we are going to buy Bitcoin in a corporate structure. Because of what MicroStrategy has done, you should value us at a similar premium”.
A large number of publicly listed firms have recently started adopting the Michael Saylor Bitcoin playbook and adding Bitcoin to their balance sheet. Semler Scientific, for example, also adds Bitcoins periodically. However, its stock price has recently declined sharply due to the company’s poor financial performance.
Long Bitcoin Bets on the Rise
Long BTC bets have risen recently, as blockchain analytics firm Glassnode reports a notable increase in Bitcoin’s Long-Term Holder (LTH) realized price to $45,340. This rise reflects the aging of coins purchased at higher price levels, around $90,000–$100,000, as they transition into long-term holding status.
#Bitcoin's LTH realized price has climbed to $45.34K -reflecting the aging of coins bought around $90K–$100K into long-term status. With the 155-day cut-off, buyers from Dec '24 are now LTHs, gradually lifting the cohort’s cost basis. pic.twitter.com/BZghQmnQLi
— glassnode (@glassnode) May 14, 2025
The shift aligns with the 155-day cut-off, meaning buyers from December 2024 are now classified as Long-Term Holders. This transition is gradually raising the LTH cohort’s cost basis.
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