Wall Street’s hottest debate pits Jim Chanos against Michael Saylor
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Wall Street’s hottest debate pits Jim Chanos against Michael Saylor
Short seller Jim Chanos is ramping up his criticism of Wall Street’s most popular bitcoin trade. Chanos has made a career out of betting against companies he believes are wrongly valued. Michael Saylor has turned a business intelligence software firm into a bitcoin juggernaut by using a combination of debt and equity to add tons of the world’s largest cryptocurrency to his company’s balance sheet. Saylor’s counterargument to Chanos’s skepticism is that shares of Strategy are easier to own and buy than bitcoin or bitcoin exchange-traded funds due to compliance and regulatory rules. The escalating war of words has captivated Wall Street as the two lob shots at one another via TV networks such as CNBC.
“It makes kind of no sense,” Chanos said in a recent interview on Bloomberg’s “Odd Lots” podcast, the latest in a series of public comments taking aim at the market frenzy surrounding Saylor’s company.
Saylor has turned a business intelligence software firm into a bitcoin juggernaut by using a combination of debt and equity to add tons of the world’s largest cryptocurrency to his company’s balance sheet.
Strategy now holds 597,325 bitcoins worth roughly $64 billion as of June 30, making it the largest corporate holder of the digital asset. And the stock of his company has soared 210% over the past year — well above the 80% gain of bitcoin itself as well as a 13% gain for the S&P 500.
The main concern about all this, which Chanos continues to hammer home in TV appearances and podcasts, is that Strategy should not be valued higher than the underlying asset it owns, and that investors should simply buy bitcoin instead of stock in a company buying bitcoin.
Chanos’s views carry weight on Wall Street. He has made a career out of betting against companies he believes are wrongly valued, and is most famous for predicting the downfall of Enron in 2001.
Chanos & Co. founder and managing partner Jim Chanos at the 2025 Sohn Investment Conference, in New York, on May 14. REUTERS/Jeenah Moon · REUTERS / Reuters
Saylor’s counterargument to Chanos’s skepticism is that shares of Strategy are easier to own and buy than bitcoin or bitcoin exchange-traded funds due to compliance and regulatory rules.
Proponents of his approach also argue that Strategy’s stock trades at such a rich price to bitcoin because investors believe the company will continue to suck up more of the asset’s finite supply of 21 million units.
“If you want to 10x your money, you buy bitcoin,” Saylor said in May at a conference convened to show other firms how to adopt his so-called “bitcoin treasury” strategy.
“If you want 100x your money, you buy bitcoin with someone else’s money. If you want to 1000x your money, you buy bitcoin with someone else’s money and then you leverage the bitcoin.”
‘Financial gibberish’
The escalating war of words between Chanos and Saylor has captivated Wall Street as the two lob shots at one another via interviews with TV networks such as CNBC and Bloomberg.
“I don’t think he understands what our business model is,” Saylor has said of Chanos, predicting that “if our stock rallies up, he’s going to get liquidated and wiped out.”
Chanos has said of Saylor that he “is a wonderful salesman, but that’s what he is: He’s a salesman … I call it financial gibberish.”