Michael Saylor just said something he’s avoided for five years: MicroStrategy Inc (NASDAQ:MSTR) might sell Bitcoin (CRYPTO: BTC) “in the interest of shareholders.” The comment stunned a market conditioned to believe the company would hold forever — and instantly ignited a fresh wave of speculation about what the move really means.
Track BTC price here.
And if you ask Jim Cramer, this might not be capitulation. It might be the setup for what he calls the “squeeze of a lifetime.”
The Unexpected Pivot That Shook Bitcoin Traders
MicroStrategy — the company holding roughly 650,000 Bitcoin, more than $55 billion worth at current market prices — now trades at a market cap nearly $10 billion below the value of its Bitcoin treasury. That valuation inversion is a fact, and it’s the first significant sustained break below net asset value the company has ever faced.
Add in $8.2 billion in debt, $7.8 billion in preferred stock obligations and a stock that’s collapsed 57% since Oct. 6, and the pressure looks real.
That’s where Cramer jumps in. Posting on X, he wrote that Saylor is “a master poker player” and could “engineer a squeeze of a lifetime by going the opposite of what he says.” That’s opinion — not fact — but it’s a powerful storyline circulating in trader circles.
Read Also: If You’re Expecting A Bitcoin Bear Market In 2026, You Have It Wrong, Grayscale Says
A Threat, A Bluff, Or A Trap Door?
The possibility of selling Bitcoin changes the psychology of the stock. Shorts now face two risks: if Saylor sells, panic could push $BTC and MSTR sharply lower — but if he doesn’t, and instead buys or simply delays, the NAV gap itself becomes the squeeze fuel. Either scenario is combustible when nearly a quarter of the float is sold short.
Is Saylor bluffing? Is he buying time? Or is he daring traders to bet against him one more time?
What’s Clear
There are two asset classes here: Bitcoin and belief. Saylor controls both. And as long as the market can’t tell whether he’s holding or baiting, the game isn’t over — it’s just getting volatile.
Read Next:
Bitcoin Roars Back To $91,000: ‘Counter-Trend Rally’ Is Coming, But Be Patient, Analyst Says
Photo: PJ McDonnell on Shutterstock.com
$BTCBitcoin – United States dollar$91408.005.91%OverviewMSTRStrategy Inc$186.448.76%Market News and Data brought to you by Benzinga APIs
