James Chanos, the renowned short-seller, identified Strategy as one of the greatest pure arbitrage opportunities he has ever seen, with an $80 billion actionable spread between the company’s stock and its Bitcoin holdings. Strategy owns approximately 847,363 BTC, worth about $54 billion at Bitcoin’s August price of around $64,000. Chanos built a short position in MSTR while buying Bitcoin from late 2024, betting that MSTR’s premium over its Bitcoin holdings would contract. MSTR’s multiple to its Bitcoin holdings compressed from above 3x to approximately 1.23x by November 2025, allowing Chanos to close out his position on November 7.
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