Picture this: Bitcoin is down hard, trading under $95,000 after touching six figures just weeks ago. The entire crypto market is bleeding. And in the middle of this storm, one man quietly clicks “buy” on another billion dollars worth of Bitcoin. Not a hedge fund, not a nation-state, just Michael Saylor and his company Strategy (formerly MicroStrategy) doubling down again.
I’ve been watching this story unfold for years now, and honestly? Every single time I think “this is it, he’s finally gone too far,” something wild happens. So when I saw the stock gap down to $192 on Monday morning, its lowest level since last October, I had to dig deeper. Is this the moment the Strategy experiment finally cracks, or are we watching the greatest contrarian play in modern market history?
The Latest Move That Raised Everyone’s Eyebrows
Last week, while most traders were panicking and futures open interest was collapsing, Strategy scooped up 8,178 BTC for roughly $835 million. That brought their total stash to an absurd 649,870 Bitcoins, acquired at an average price of about $74,433 per coin.
Let that sink in for a second. They now hold more Bitcoin than most countries. Their total holdings are worth north of $61 billion right now, even after the crash, and they’re still sitting on unrealized gains because their cost basis is around $48 billion total. In Saylor’s words, they’ve achieved a Bitcoin Yield of 27.8% year-to-date in 2025. Yeah, he actually uses that term unironically.
“We are ₿uying.”
– Michael Saylor, November 14, 2025
Three words. A meme picture. And somehow that was enough to make half of finance Twitter lose their minds.
Why the Stock Is Getting Crushed Anyway
Here’s the brutal truth: the market doesn’t care about long-term vision when margin calls are hitting. MSTR stock has lost $72 billion in market cap since its August peak, sliding from $128 billion to around $57 billion today. That’s not a correction. That’s a full-blown nightmare for anyone who bought the top.
The company’s market Net Asset Value (mNAV), that fancy ratio everyone uses to measure how much premium (or discount) the stock trades at relative to its Bitcoin holdings, has crashed from over 3x to barely 0.94x. Translation? The market is now pricing Strategy shares as if the Bitcoin is worth less than book value. That almost never happens unless people genuinely believe liquidation is coming.
- Bitcoin formed a textbook death cross on the daily chart
- Futures open interest dropped from $94B to $64B in weeks
- MSTR broke below the key 61.8% Fibonacci retracement at $214
- Double-top pattern on weekly with neckline at $231 now acting as resistance
- ADX trending above 40 – strong bearish momentum confirmed
Technically, everything looks ugly. Really ugly.
But Wait – Saylor Might Actually Be Right This Time (Again)
Look, I’m not drinking the Bitcoin-maximalist Kool-Aid here, but the man has been ridiculously right for five years straight. Every time people screamed “this is the top,” he kept buying, and every time Bitcoin eventually proved him correct. Maybe not on the timeline anyone wanted, but eventually.
His core argument hasn’t changed: Bitcoin is digital gold with a fixed supply and growing institutional demand. The recent crash, in his view, is just deleveraging, over-leveraged traders getting washed out. Once that finishes, the path of least resistance is higher. He said exactly that on television last week while everyone else was predicting $70k.
And here’s the part that actually keeps me up at night: the supply side is getting tighter literally by the day. Miners are selling less after the halving cycles, ETFs are absorbing whatever is left, and large holders (whales) aren’t spending. If demand ever comes back even modestly, the squeeze could be historic.
So Will MSTR Actually Recover?
Short answer: nobody knows. Anyone who tells you they do is selling something.
But let’s look at realistic scenarios.
Bull case: Bitcoin stabilizes around current levels, then grinds higher into 2026 as the deleveraging finishes and new capital enters (ETFs, corporate treasuries, maybe even nation-state buying). MSTR’s mNAV expands again to 2x or higher, stock easily doubles from here even if Bitcoin only hits $150k.
Base case: We chop sideways for months. Bitcoin trades between $80k and $120k while the market figures out interest rates and regulatory clarity. MSTR drifts, maybe retests the low $100s, but the Bitcoin hoard keeps growing and the company stays solvent.
Bear case: Bitcoin breaks below $80k decisively and liquidates a wave of corporate holders. Margin pressure forces some sales (not necessarily Strategy, but others), and MSTR gets caught in the crossfire. Stock could absolutely see $125 or lower.
| Scenario | BTC Price Target | MSTR Price Target | Probability (my guess) |
| Bull | $150,000+ | $400+ | 30% |
| Base | $80k–$120k | $200–$300 | 50% |
| Bear | <$80,000 | <$150 | 20% |
The One Chart That Actually Matters
Forget the stock chart for a second. The only chart that has ever mattered for MSTR is the long-term Bitcoin price versus their average acquisition cost. As long as Bitcoin stays above ~$74,000 on average, they’re fine. Below that for an extended period? Then we have real problems.
Right now we’re still $20,000 above their average buy price. That’s the margin of safety Saylor keeps talking about. It’s shrinking, sure, but it’s still there.
What I’m Watching Next
- Can Bitcoin hold the $90,000 zone? A weekly close below that flips the macro structure bearish.
- Is futures open interest stabilizing or still collapsing?
- Any sign of forced selling from other corporate holders?
- Does MSTR announce another capital raise soon? (They usually do when the stock is “cheap”)
- The mNAV – if it starts creeping back above 1.2x, the sentiment is shifting.
Bottom line? This is still the highest-conviction bet I’ve ever seen one person make with shareholder money. It’s either going to go down as one of the greatest wealth creation stories in history or one of the most spectacular blowups.
And honestly? After watching Saylor be right for half a decade while everyone else panicked, I’m not betting against him just yet.
The dip buyers who loaded up at $192 this week might look like geniuses in two years, or they might be the last ones holding the bag. That’s the beauty (and terror) of this trade.
Either way, one thing is certain: Michael Saylor isn’t blinking. And until Bitcoin actually trades below his cost basis for a sustained period, the Strategy story probably isn’t over.
Whether that’s comforting or terrifying kind of depends on which side of the trade you’re on.
Note: None of this is financial advice. Markets can stay irrational longer than you can stay solvent, especially when Bitcoin and leverage are involved. Do your own research.
