Disclaimer: The analyst who wrote this article owns shares in Strategy.

Jim Chanos, the founder of Kynikos Associates who famously shorted U.S. energy giant Enron before it collapsed in 2001, has set his sights on Strategy (MSTR), arguing the bitcoin (BTC)-buying company’s premium valuation over its holdings of the largest cryptocurrency is unjustified.

Chanos has placed a bet against Strategy’s stock by shorting it while maintaining a long position in bitcoin itself, aiming to profit if the company’s premium valuation shrinks. In shorting, a trader borrows stock, sells it and hopes the price falls enough for them to buy it back in time to return to the lender while leaving them with a profit.

The investor has earned a reputation for spotting corporate frauds and overvalued companies. Enron, once a major U.S. energy firm, collapsed amid massive accounting fraud, wiping out billions in value and sending top executives to prison, becoming a lasting symbol of corporate scandal.

He criticized the financial maneuvers of Strategy Executive Chairman Michael Saylor, who has sold convertible debt and preferred shares to raise money to buy more bitcoin, calling them “financial gibberish” and warning that the sales create risks for shareholders. Strategy has accumulated more than 600,000 bitcoins, far surpassing its closest competitors.

In a debate on the We Study Billionaires podcast, Chanos clashed with Pierre Rochard, CEO of Bitcoin Bond Co. and a well-known bitcoin advocate, over Strategy's roughly 1.9 times net asset value premium.

According to Chanos, the company offers nothing unique beyond owning bitcoin, and contends the premium should disappear as more than 140 other firms worldwide, including MARA Holdings (MARA), Riot Platforms (RIOT) and Metaplanet (3350), pursue similar treasury strategies.

Rochard, however, sees Strategy’s large bitcoin stash and first-mover advantage as key strengths. He argued the company can raise significant debt without diluting shareholders and that investors view Strategy as a leveraged play on BTC, akin to holding a call option for potential upside. Rochard also suggest that crypto-friendly policies under the administration of President Trump could attract more investment into the industry, boosting Strategy’s appeal.

While Chanos insisted direct bitcoin ownership is safer and simpler, Rochard countered that Strategy’s size enables it to leverage more efficiently than individual investors.

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