Wall Street’s hottest debate pits Jim Chanos against Michael Saylor
- - - Wall Street's hottest debate pits Jim Chanos against Michael Saylor
David HollerithJuly 4, 2025 at 3:00 AM
One of Wall Street's most prominent skeptics, short seller Jim Chanos, is ramping up his criticism of Wall Street's most popular bitcoin trade: Michael Saylor's Strategy (MSTR).
"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."
Neither Chanos nor Saylor responded to Yahoo Finance requests for comment.
So far in 2025, bets against Saylor have not worked out. Investors betting against Strategy over the last month have seen $3.6 billion in losses, according to short seller data provider S3 Partners.
Michael Saylor at the Bitcoin Conference 2023, in Miami Beach. REUTERS/Marco Bello (REUTERS / Reuters)
Chanos isn't Strategy's only critic. Investors filed two separate lawsuits in May and June in a federal court in Virginia, both of which included allegations that Strategy misled them about how the volatility of bitcoin could affect the stock.
Some analysts have also raised concerns. Monness, Crespi, Hardt & Co analyst Gustavo Gala said in a recent series of notes to clients that Strategy's premium will likely come down as fixed income investors have shown limited interest in the company's convertible debt and preferred shares used to fund its bitcoin purchases, writing in early June that Strategy has "a limited runway" to continue its approach.
Gala noted that there is a growing concentration of companies pursuing a "copycat BTC Treasury Strategy." Dozens of other companies, from a media firm controlled by President Trump's family to meme stock poster child GameStop (GME), have piled into bets similar to the blueprint laid out by Saylor.
And "all of these compete for an ostensibly similar pool of capital," Gala wrote in a note Tuesday.
Over the first half of 2025, public companies collectively added 245,191 bitcoins to their balance sheet, more than twice as much as bitcoin holding ETFs over the same period, according to data provider Bitcoin Treasuries.
The latest big name to enter the crypto treasury game is Fundstrat founder Tom Lee, who is joining bitcoin mining firm BitMine Emersion Technologies (BMNR) as chairman after joining several institutions in helping this company raise $250 million to launch an ether (ETH-USD)-focused treasury strategy.
BitMine's stock price has taken off since the June 30 announcement, climbing more than 30 times its pre-announcement price of $4.26.
Short sellers have had far better luck betting against imitators of Saylor as opposed to Saylor's actual company.
For the month of June, they earned $549 million betting against four of Strategy's largest imitators, according to S3.
David Hollerith is a senior reporter for Yahoo Finance covering banking, crypto, and other areas in finance. His email is david.hollerith at yahoofinance.com.
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