Right now, Strategy is underwater.
The buffer between the current
#Bitcoin price and Saylor’s average entry is down to just a few hundred dollars per BTC. At one point overnight, the entire position was negative.
And what did Saylor do?
👉 He bought more BTC last week — at prices ABOVE the current market.
I’ve been tracking this story since my December projection. Why? Because Strategy is system-relevant for crypto.
📉 Facts first:
$MSTR stock: –75% from ATH8 consecutive red monthsBitcoin position: near breakeven, briefly underwater
⚠️ Important clarification
There is NO classic margin call.
❌ No Bitcoin is posted as collateral
❌ No lender can force-liquidate BTC
But… there ARE three scenarios where selling BTC could still become necessary.
🔑 Trigger 1: The Put Dates (Convertible Notes)
Strategy issued billions in convertible bonds.
If $MSTR trades below the conversion price, bondholders won’t convert to equity — they’ll demand cash repayment instead 💵.
📆 First major put date: Q3 2027
📉 Current $MSTR price: well below conversion levels
That’s a ticking clock.
🔑 Trigger 2: The Cash-Flow Squeeze
Strategy has five preferred-share series, paying dividends up to 11.25% 😬
💸 Annual dividend obligations
⬆️ Far exceed operating income
At the current burn rate, cash reserves last until ~mid-2028 — exactly when the put dates hit.
That overlap matters.
🔑 Trigger 3: The Flywheel Reverses
The old model was simple:
🔁 Issue shares → Buy BTC → BTC up → Stock up → Repeat
Now?
⚠️ mNAV is close to 1
⚠️ New share issuance causes immediate dilution
Strategy has even admitted that under certain conditions, it may pause new share issuance — with legal “escape clauses.”
That’s the flywheel slowing… maybe reversing.
🧠 Market Signals
Polymarket now shows bankruptcy odds for StrategyInvestor confidence is fragileBitcoin volatility makes timing critical
I don’t see the real danger in 2026.
📍 Q3 2027 is the moment of truth.
If:
#Bitcoin is weak
#MSTR stays below conversion prices
Then Saylor needs a Plan B.
📊 Tomorrow: Q4 earnings.
That’s when we’ll see how Strategy explains billions in unrealized BTC losses to the market.
This story is far from over.
I’m staying on it. 🤝