For five years, MicroStrategy Inc. (MSTR) has been the ultimate Bitcoin believer. Michael Saylor turned his software company into a Bitcoin (BTC) treasury play and never looked back. Until now.
Saylor just floated the idea that MicroStrategy might sell Bitcoin "in the interest of shareholders." That's a seismic shift for a CEO who built his entire strategy around accumulating and holding forever. And Jim Cramer thinks this might not be a white flag—it could be bait.
The Numbers Behind the Drama
MicroStrategy owns roughly 650,000 Bitcoin, currently worth more than $55 billion. Sounds great, except the company's market cap now sits nearly $10 billion below the value of that Bitcoin stash. That's a sustained break below net asset value, something the stock has never really faced before.
Layer in $8.2 billion in debt, $7.8 billion in preferred stock obligations, and a stock that's down 57% since early October, and you've got a pressure cooker. The valuation inversion is real, and the market is starting to ask uncomfortable questions.
Cramer's Theory: The Ultimate Poker Move
That's where Cramer steps in. Writing on X, he called Saylor "a master poker player" who could "engineer a squeeze of a lifetime by going the opposite of what he says." It's speculation, sure, but it's not coming from nowhere.
Here's the setup: nearly a quarter of MicroStrategy's float is sold short. If Saylor actually sells Bitcoin, panic could hammer both the stock and Bitcoin itself. But if he doesn't—if he delays, or worse, starts buying again—that valuation gap becomes fuel for a short squeeze. Either way, someone's getting burned.
Is This a Threat or a Trap?
The mere possibility of selling changes everything. Shorts now face a double-edged sword. Saylor holds the cards, and the market has no idea what he's actually planning. Is he bluffing to shake out weak hands? Buying time to restructure? Or daring traders to bet against him one more time?
What's certain is this: there are two assets at play here—Bitcoin and belief. Saylor controls both. And as long as the market can't tell whether he's holding or baiting, the volatility isn't going anywhere. The game, as they say, is far from over.