Jim Chanos was right about Strategy — just not patient enough

Short-seller Jim Chanos was right to be bearish about Strategy (formerly MicroStrategy) in late 2024, but even he, one of Michael Saylor’s biggest critics, didn’t hang on long enough.

Chanos took a victory lap with his short MSTR, long bitcoin ($BTC) pair trade on November 7, 2025, walking away with a respectable profit. He also predicted the substantial drop in optimism among investors in Michael Saylor’s common stock.

However, he was also too early to celebrate his accuracy and could have made much more if he’d just held on.

In his private fund, the Chanos & Co. founder started selling short shares when the multiple-to-Net Asset Value or “mNAV” of Strategy exceeded 2.5x the value of its $BTC. Based on historical charts, that means that Chanos started shorting MSTR during the October-November 2024 timeframe.

During those two months, the worst price Chanos could have sold short was near $168 per share. If he’d timed the pico top, he could have got close to $543.

Chanos’ target was too conservative

By December 2024, Chanos broadcasted his trade publicly at Chanos & Co.’s Bears in Hibernation conference. He also set a target to exit his trade: the mNAV spread of MSTR to its $BTC holdings declining to 1.25x.

Fast-forward to yesterday’s close, and he could have covered all of those sales at just $136 per MSTR. That would have generated at least a 19% profit or up to a 75% gain.

Most importantly, MSTR’s basic mNAV premium is now just 0.74x, a staggering 40% of extra winnings that Chanos left on the table when he walked away at a basic mNAV of 1.23x.

Indeed, his long $BTC hedge as the second leg of his pair trade, probably wouldn’t have cost him much out of the substantial drop in MSTR — a lavish 19-75% drop that he enjoyed — and might have even earned him some extra cash.

Specifically, in October and November 2024, $BTC traded as low as $58,864 and as high as $99,860. At yesterday’s Nasdaq close, $BTC was trading at $67,500.

For Chanos, that translates into a 14% gain at best to a 32% loss at worst on his $BTC hedge.

Putting it all together

Both legs of the trade — short MSTR, long $BTC — are captured in the single mNAV figure which declined from Chanos’ exit at 1.23x on November 7, 2025 to today’s 0.74x.

In other words, had the Chanos & Co. founder held the position for seven more months, his hedged bet would have paid him an extra 40%.

The reason the trade has continued to pay is the same reason Chanos put it on. Strategy’s mNAV, the premium that investors pay for MSTR to the $BTC on its balance sheet, has never recovered its 2024 euphoria.

For one brief glorious day on November 20, 2024, investors paid 3.4x more for MSTR than the $BTC it held at the time.

Saylor peaked just as Chanos bet against him. By the start of 2025, Strategy’s mNAV was already well below 2x.

Within months, it sank below 1x. Strategy eventually introduced a redefined mNAV to temporarily boost the notional figure above 1x, its so-called enterprise value mNAV, yet its original, basic mNAV continued to decline.

Strategy’s basic mNAV hasn’t rallied above 1x since November 2025.

Chanos bet the euphoira would fade. It has. He simply stopped collecting on his prediction before the market finished proving him right.