BitcoinMarkets
|3 min ReadHow Jim Chanos Outplayed Michael Saylor: Short MSTR, Long Bitcoin
Maya Chen
Senior Analyst
Published
Jan 16, 2026
Jim Chanos just pulled off one of Wall Street’s most elegant trades — betting against Michael Saylor’s company while staying bullish on Bitcoin itself. The veteran short-seller closed his long-running position against MicroStrategy (now rebranded as Strategy), reportedly doubling his money by shorting MSTR stock while holding Bitcoin long.
His thesis was simple: MSTR had become an overpriced proxy for Bitcoin. By shorting the stock and buying BTC directly, Chanos bet the company’s premium over its crypto holdings would shrink — not that Bitcoin itself would fall.
It worked perfectly. When he entered the trade in November 2024, MSTR traded at roughly 3 times its net Bitcoin asset value. By the time he exited in November 2025, that multiple had collapsed to just 1.23x, a 23% premium over its BTC stack. Meanwhile, Bitcoin’s price itself rose around 25% during the same period. Chanos made money on both sides.
Short the stock, long the coin
Strategy, formerly MicroStrategy, now operates as a “digital asset treasury” company — essentially a leveraged Bitcoin holding vehicle disguised as a software firm. It holds about 84 million enterprise value, giving it that volatile mNAV multiple Chanos targeted.
When he launched the trade, Chanos described it bluntly at his annual conference: “Sell MSTR and buy Bitcoin — you’re buying something for one dollar and selling it for two-fifty.” The logic: Saylor’s firm kept issuing new shares to buy more Bitcoin, diluting shareholders while boosting its exposure. To Chanos, that was the trade signal itself.
By Friday morning, the founder of Chanos & Co. had closed the position, locking in roughly a 100% gain. His post-trade victory lap on social media drew over a million views.
A mirror of Saylor’s own playbook
The irony wasn’t lost on him. Chanos’ strategy — sell the company, buy the Bitcoin — was effectively what Saylor had been doing all along. The difference: one did it for leverage, the other to arbitrage it.
Saylor’s “buy BTC on leverage” mantra has drawn equal parts admiration and ridicule on Wall Street. Chanos publicly called the idea “ridiculous” and “financial gibberish” during interviews with CNBC, arguing that MSTR’s value was being inflated by speculative enthusiasm rather than fundamentals.
As Strategy continued selling billions in stock and preferred shares to fund more Bitcoin purchases, Chanos’ conviction only grew stronger. When the company’s premium finally collapsed, it validated his core thesis: Bitcoin exposure is best owned directly, not through a debt-fueled corporate wrapper.
Chanos walked away with a rare double win — profit on the short, profit on the long, and a clean reminder to investors chasing proxy plays: sometimes the simplest trade is to skip the middleman.
Disclaimer: This document is intended for informational and entertainment purposes only. The views expressed in this document are not, and should not be taken as, investment advice or recommendations. Recipients should do their own due diligence, taking into account their specific financial circumstances, investment objectives and risk tolerance, which are not considered here, before investing. This document is not an offer, or the solicitation of an offer, to buy or sell any of the assets mentioned.