Jim Chanos Bets Against MicroStrategy Stock While Going Long on Bitcoin

Legendary short-seller Jim Chanos, known for exposing Enron’s collapse, is now executing a long-short trade involving bitcoin and MicroStrategy (MSTR), the largest corporate bitcoin holder.

During the Sohn Investment Conference in New York, Chanos revealed to CNBC that his firm is shorting MicroStrategy shares while simultaneously buying bitcoin outright. “We’re selling MicroStrategy stock and buying bitcoin,” he explained. “It’s like buying something for $1 and selling it for $2.50.”

Since 2020, MicroStrategy has built a substantial bitcoin position by issuing debt and equity, currently holding around 568,840 BTC at an average purchase price near $69,287. This has positioned the company as a proxy for bitcoin investors.

MicroStrategy’s stock price has surged approximately 3,500% over five years to $416 per share, pushing its market cap to roughly $115 billion. However, Chanos argues that the stock’s rise has outstripped bitcoin’s actual price gains, driven more by speculative trading than by intrinsic value.

He believes other firms trying to replicate MicroStrategy’s bitcoin buying approach face similar valuation risks, warning investors to be cautious about inflated expectations.