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Reading: How Jim Chanos outplayed Michael Saylor: brief MSTR, lengthy BTC
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Michigan Post > Blog > Crypto & Web 3 > How Jim Chanos outplayed Michael Saylor: brief MSTR, lengthy BTC
Crypto & Web 3

How Jim Chanos outplayed Michael Saylor: brief MSTR, lengthy BTC

By Editorial Board Published November 10, 2025 4 Min Read
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How Jim Chanos outplayed Michael Saylor: brief MSTR, lengthy BTC

How Jim Chanos outplayed Michael Saylor: brief MSTR, lengthy BTC

Wall Avenue cynic Jim Chanos has closed out his extensively publicized and controversial guess in opposition to Michael Saylor’s Technique (previously MicroStrategy), seemingly doubling his cash by way of short-selling the corporate’s MSTR widespread inventory.

To be actual, the short-seller constructed a pair commerce of brief MSTR and lengthy bitcoin (BTC).

Reasonably than betting that the worth of MSTR would decline on an absolute USD foundation, Chanos merely guess that the premium of MSTR would decline in opposition to BTC.

Technique is the world’s largest digital asset treasury (DAT) firm, a class of publicly-traded firms that purchase crypto tokens utilizing monetary leverage fairly than specializing in conventional gross sales of services or products.

The corporate owns roughly $66 billion value of BTC and trades at an $84 million enterprise worth (market cap plus professional forma web debt together with preferreds), a beneficiant 1.27x multiple-to-net asset worth (mNAV).

Nonetheless, that mNAV has declined considerably since Chanos entered his commerce.

After getting into his two-legged place in November 2024 to specific doubt that MSTR would outperform BTC, the billionaire Chanos & Co. founder closed out his on Friday morning after incomes roughly 100%.

His victory lap on social media earned over 1 million impressions.

Quick MSTR, lengthy BTC

Chanos profited from MSTR’s mNAV decline from above 3x in November to a possible common round 2.5x when he shared his thesis at his annual convention in December 2024.

By the point he absolutely closed his commerce, its mNAV had declined to 1.23x — a mere 23% premium to its BTC holdings.

Over the identical interval, the second leg of his commerce had additionally grown in revenue. Since November 2024, the worth of BTC has elevated roughly 25%.

In different phrases, not solely did Chanos double his cash shorting MSTR, he additionally earned roughly 25% from BTC appreciation. Profiting on each legs of his commerce, the household workplace fund supervisor has cemented his place as probably the most profitable critic of Saylor.

Promoting MSTR to purchase BTC, identical to Saylor

Chanos earned instant vitriol from Saylor followers just like the self-named Irresponsibly Lengthy MSTR group for broadcasting a bearish funding thesis on Technique on the 2025 New York Sohn Funding Convention.

On quite a few televised and social media interviews, Chanos described his bearishness on Technique sustaining a lofty mNAV.

He beforehand described his technique as “selling MicroStrategy stock and buying BTC and basically buying something for $1 selling it for $2.50.”

He additionally known as Saylor’s description of buying BTC on leverage “ridiculous” and “financial gibberish.”

Actually, he characterised his commerce as merely replicating the actions of Saylor himself: promoting MSTR to purchase BTC.

Chanos repeatedly famous that Technique’s dilutive gross sales of MSTR — aggressively promoting down its personal mNAV to purchase BTC — was the commerce catalyst that satisfied him to provoke his two-pronged commerce within the first place.

Though Technique has offered a number of billion {dollars} value of most popular shares that don’t instantly dilute MSTR, it’s raised the overwhelming majority of its capital from MSTR gross sales.

Protos reached out to Chanos for remark however didn’t obtain a reply previous to publication time.

TAGGED:BTCChanosJimLongMichaelMSTRoutplayedSaylorShort
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