Jim Chanos Sees Big Short in Saylor’s Strategy, Others See Risks

Buy Bitcoin, short Michael Saylor’s Strategy. That’s the latest call from legendary short-seller Jim Chanos, who sees the arbitrage play as a no-brainer. Others aren’t so sure.

The trade has long been on the radar of Wall Street hedge funds, drawn to the premium Strategy’sshares enjoy relative to the value of the company’s Bitcoin holdings — a gap that topped 200% last year. The discrepancy stems from Saylor’s self-styled Bitcoin treasury strategy, through which he has tapped capital markets to buy more and more of the world’s biggest cryptocurrency, in turn attracting billions of dollars from retail ...