Cliff Asness Sides with Jim Chanos in Critique of Michael Saylor’s Bitcoin-Fueled Debt Strategy

A heated financial debate is unfolding on Wall Street as prominent hedge fund figure Cliff Asness lends his support to short seller Jim Chanos in a growing critique of Michael Saylor’s aggressive Bitcoin investment strategy.

At issue is Saylor’s firm—now known as Strategy, formerly MicroStrategy Inc.—and its use of approximately $10 billion in convertible debt to acquire Bitcoin. Saylor, the company’s executive chairman and an outspoken crypto advocate, maintains that this debt carries minimal risk. According to him, it can be repaid with company shares and isn’t likely to be called in, even if Bitcoin prices drop.

But both Chanos and Asness are challenging that assessment. In a recent post on X (formerly Twitter), Asness firmly stated that Chanos “is of course right,” aligning himself with the view that Strategy’s approach glosses over the financial liabilities it has incurred.

Chanos, in previous interviews, has gone further—labeling Saylor’s valuation model “financial gibberish” and pointing out that the company’s market capitalization appears to far outpace the value of its actual Bitcoin reserves. He has even proposed a trade strategy: short Strategy’s stock while buying Bitcoin directly, capitalizing on what he sees as a mispricing in the market.

Saylor, undeterred, has waved off the criticism, arguing that Chanos simply misunderstands the mechanics and vision behind Strategy’s crypto play.

This escalating dispute is about more than just one company’s balance sheet. It underscores a broader divide in the financial world—between traditional risk-averse investment thinking and the bold, often volatile strategies emerging in the era of digital assets.