MSTR Underperforms Bitcoin by Widest Margin Since 2024, Holding ~847,000 BTC
Claire Weston
Strategy's stock (MSTR) has underperformed Bitcoin by nearly 18 percentage points over the past month — the widest gap since March 2024 — as the market reassesses the sustainability of a leveraged-Bitcoin proxy model.
How bad is the underperformance?
Over the past month MSTR fell 36.5% while Bitcoin dropped 18.5% — a gap of nearly 18 percentage points.
Year-to-date, MSTR is down 31.6% versus Bitcoin's 29.6% decline. The gap has narrowed but remains negative.
This means → owning MSTR has delivered worse returns than simply holding Bitcoin — leverage amplified losses on the way down.
Why is the market losing faith?
Strategy's thesis is straightforward: issue stock and debt to buy Bitcoin, betting that BTC appreciates faster than financing costs compound.
Three forces are now squeezing that thesis simultaneously: equity dilution (constant new share issuance), premium compression (the stock's premium to net asset value is shrinking), and rising macro volatility.
In plain terms = the company is essentially a leveraged Bitcoin fund. Once the market doubts the leverage can hold, the stock falls harder than the coin itself.
How long can the cash last?
Dollar cash reserves have fallen 36% since early 2026 to $1.4 billion.
In May the company repurchased $1.5 billion in zero-coupon convertible senior notes due 2029, further draining the cash buffer.
CryptoQuant head of research Julio Moreno says cash needs to be rebuilt to roughly $2.8 billion — enough to cover 24 months of preferred-stock dividends. This means → current cash sits at only half the safety threshold.
What is happening to the preferred and common stock?
STRC preferred shares fell to $82.50 last week — a record 17.5% discount to the $100 par value.
Common stock MSTR also hit its lowest level since May 2024. Fear has spread from the preferred to the common.
This reflects a market pricing in doubt not just about near-term coin volatility, but about the entire financing structure's viability.
Is the company still buying Bitcoin — and with what money?
Between June 15 and 21 Strategy purchased another $34.9 million in Bitcoin, bringing total holdings to roughly 847,363 BTC.
The purchase was funded entirely by selling Class A common shares — the third consecutive week of common-equity financing.
In plain terms = the company pledged to shift toward perpetual preferred stock as its primary funding tool, yet it keeps selling common shares to buy coins — exactly the dilution the market fears.
What is the key variable to watch?
Analyst Marc Gerstein flagged "red flags": the company leans too heavily on unreliable historical performance, and the model's sheer complexity is itself a negative.
The core variable is singular: can MSTR maintain its buying pace without further large-scale equity dilution?
If the answer is no, the stock's discount to Bitcoin may keep widening — the leveraged-proxy thesis is under a live stress test.
Content is for reference only, not financial advice.