Short Seller Jim Chanos Calls Out Michael Saylor for Skipping Bitcoin Dip Buy

Famed short seller Jim Chanos has taken aim at MicroStrategy chairman Michael Saylor after noticing the company failed to buy Bitcoin during a major market dip. In a recent post on X, Chanos mocked Saylor for not acting on what many consider an ideal buying opportunity, questioning why the company that consistently touts its Bitcoin-accumulation strategy would sit out during a sharp correction.

Chanos pointed out the apparent contradiction, asking, “Isn’t that when they should be buying more?” His comments quickly drew attention, especially given his history of skepticism toward MicroStrategy’s valuation relative to its Bitcoin holdings. Earlier this year, Chanos revealed that he had shorted MicroStrategy stock while simultaneously holding Bitcoin, arguing that the company’s market value carried an outsized premium above its “modified NAV,” or the net value of its BTC reserves. He went as far as calling parts of Saylor’s financial model “gibberish,” and his thesis ultimately proved accurate as MicroStrategy stock sharply underperformed Bitcoin itself.

The investor, well known for his legendary short against Enron, recently disclosed that he unwound this hedged trade after the premium collapsed. While he hasn’t shared exact returns, the move appears to have been significantly profitable.

Meanwhile, Saylor has repeatedly emphasized MicroStrategy’s commitment to ramping up Bitcoin purchases. Just last week, the company announced it had added another $836 million worth of BTC. But Chanos’s criticism highlights a growing concern: skipping the recent price correction raises questions about whether MicroStrategy’s ability to continue aggressive accumulation is weakening. If the company truly plans to accelerate purchases, observers wonder why it passed on one of the most attractive dips in months.

As Bitcoin markets remain volatile, both critics and supporters are watching MicroStrategy closely. Chanos’s latest remarks add more pressure on Saylor to prove that the firm’s long-term Bitcoin strategy still has the financial firepower to continue.