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Reading: How Jim Chanos outplayed Michael Saylor: short MSTR, long BTC
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Mycryptopot > Market > How Jim Chanos outplayed Michael Saylor: short MSTR, long BTC
Market

How Jim Chanos outplayed Michael Saylor: short MSTR, long BTC

November 16, 2025 4 Min Read
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Wall Road cynic Jim Chanos has closed out his extensively publicized and controversial wager towards Michael Saylor’s Technique (previously MicroStrategy), doubtless doubling his cash by means of short-selling the corporate’s MSTR widespread inventory.

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

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Reasonably than betting that the worth of MSTR would decline on an absolute USD foundation, Chanos merely wager that the premium of MSTR would decline towards BTC.

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

The corporate owns roughly $66 billion price of BTC and trades at an $84 million enterprise worth (market cap plus professional forma internet 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.

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After coming into his two-legged place in November 2024 to precise 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.

Brief 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.

Learn extra: Saylor to Jim Chanos: 3 ways your MSTR quick is doomed

Promoting MSTR to purchase BTC, identical to Saylor

Chanos earned speedy vitriol from Saylor followers just like the self-named Irresponsibly Lengthy MSTR neighborhood 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 “promoting MicroStrategy inventory and shopping for BTC and principally shopping for one thing for $1 promoting it for $2.50.”

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

In actual fact, 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 just a few billion {dollars} price 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.

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Reading: How Jim Chanos outplayed Michael Saylor: short MSTR, long BTC
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