So, MicroStrategy, or Strategy, or whatever they're calling themselves these days, is having a bit of a…moment. A "moment" like watching a slow-motion train wreck. Their stock, MSTR, is getting absolutely hammered. Down 40% in six months? Ouch.
Saylor's "Brilliant" Plan
Let's be real: Michael Saylor turned his company into a Bitcoin casino. And for a while, it looked like he was winning. Remember Q3 2025? A cool $2.8 billion in unrealized gains. Unrealized. As in, "Hey, look at all this money we could have if we sold our magic beans!" But now, with Bitcoin tanking below $100k, the chickens are coming home to roost.
And, offcourse, they keep buying more Bitcoin. Like a gambling addict doubling down, convinced the next spin will pay off. They even sold preferred stock to finance their addiction. Preferred stock! Raising the dividend to 10.5% just to get people to buy it. Give me a break. That’s not a good sign, people.
Is this genius-level strategy, or are we watching a slow-motion implosion? I’m leaning heavily towards the latter.
Here's a fun fact: Strategy moved over 47,000 Bitcoin to new wallets. The official line is “transfers.” Right. Just like when I “transfer” money from my bank account to a liquor store. Saylor even tweeted "HODL" with a picture of a burning ship. The guy's practically begging for a bailout.
The Walls Are Closing In
The market multiple to net asset value (mNAV) is shrinking. Jim Chanos, that legendary short seller, closed his short position on MSTR. Why? Because the mNAV is approaching 1x. Translation: "The market is starting to realize that MSTR is only worth the Bitcoin it holds." Which, if Bitcoin keeps dropping, means MSTR is worth…less.

Derivatives Monke, whoever that is, said it best: traders are "front-running the death spiral of MSTR and its eventual BTC force selling." Harsh, but probably accurate.
And the retail investors? They're starting to sweat. Sentiment on Stocktwits went from "bullish" to "neutral." That's like going from "everything's fine" to "we're all gonna die" in crypto-speak.
Then again, maybe I’m wrong. Maybe Saylor is a genius. Maybe he'll pull a rabbit out of his hat. Maybe Bitcoin will moon to a million dollars tomorrow. But let's be real, ain't gonna happen.
The Big Question
The big question is, what happens if Bitcoin keeps tanking? Does Saylor double down again? Does he finally admit defeat and start selling? And if he sells, what happens to the price of Bitcoin? It's a domino effect waiting to happen.
And what about the shareholders who bought into this whole thing? Are they just going to sit there and watch their investment evaporate? Or will they start demanding some accountability?
