Strategy Stock Is Bleeding, but Saylor Still “Won’t Back Down” From His Bitcoin Bet

There’s a moment in every bull–bear cycle when the crowd forgets the past and obsesses over the present. Strategy is living that moment right now.

Over the past year, Strategy’s stock has fallen nearly 60%, erasing billions in market value and handing ammunition to critics who’ve been waiting years for the company’s Bitcoin obsession to implode.

Zoom out, they say. The bubble popped.

Zoom out further, Strategy replies — and the story flips.

Because despite the carnage on the chart, Strategy’s Bitcoin stack is still in the green, and its five-year stock performance still embarrasses the tech giants everyone worships.

The Bitcoin Bet Still Works

According to BitcoinTreasuries.NET, Strategy acquired its Bitcoin at an average of $74,430.

With BTC still trading around $86,000, the company remains up nearly 16% on its entire position — even after months of market turbulence.

This is the part that rarely makes headlines.

Over five years, Strategy stock is up more than 500% — compared to Apple’s 130% and Microsoft’s 120%.

Even over the last two years, Strategy is up 226%, outpacing just about every major tech name in the market.

So what’s dragging the stock now?

Not Bitcoin.

Ironically: crypto traders hedging their own exposure.

How Strategy Became the Market’s Shock Absorber

In a recent CNBC interview, BitMine chairman Tom Lee explained a strange new phenomenon:

Strategy has become the easiest hedge in the entire crypto ecosystem.

Huge funds can’t easily short Bitcoin. They can’t easily hedge ETF flows. But they can absolutely short Strategy — and they are.

“The only convenient way to hedge someone’s long is to short MicroStrategy or buy puts,”

— Tom Lee, CNBC

This means Strategy stock is now absorbing market fear, options hedges, leveraged protection, and macro anxiety — even when Bitcoin fundamentals remain intact.

It is an unintended pressure valve.

A sponge for volatility.

A lightning rod for everything the crypto market can’t push directly onto BTC.

The result?

Strategy’s stock reacts to fear, not fundamentals.

The Real Risk: Not the Thesis — the Liquidity

Kyle Rodda at Capital.com notes the one scenario that truly matters:

A Bitcoin crash severe enough to force Strategy to sell.

“We are probably a long way from this,” he says — but acknowledges that this tail risk makes owning Strategy stock inherently riskier than simply owning Bitcoin itself.

Stocks can go to zero.

Bitcoin cannot go below one Bitcoin.

This is the philosophical fault line in the entire debate.

Saylor Is Not Backing Down

For Saylor, the volatility is background noise — a storm passing over a steel foundation.

“I won’t back down,”

— Michael Saylor, on X

On Nov. 17, Strategy bought 8,178 new BTC — an $835 million purchase that dwarfed its recent weekly accumulation pace.

The acquisition brings Strategy’s total stack to:

649,870 BTC

Worth nearly $56 billion at current prices.

While critics framed the dip as a failure, Strategy treated it as a clearance sale.

In Saylor’s world, price volatility is not a threat — it’s a coupon.

Digital Asset Treasuries Are Slowing, but Not Dead

The pressure on Strategy also reflects a broader slowdown across digital asset treasuries (DATs).

After October’s $20 billion liquidation event, inflows collapsed.

DAT inflows dropped from $11B in September to $2B in October — an 80% decline.

November is tracking even lower, at around $500M.

Liquidity is tightening across stablecoins, ETFs, and treasuries — the three pillars Wintermute says support the crypto market.

This is not a Strategy-specific issue.

It’s a market-wide contraction.

And Strategy, being the largest corporate Bitcoin accumulator in the world, feels the tremors most.

The Bottom Line

Strategy’s stock is bleeding.

Short sellers are crowding in.

Liquidity is drying up.

And critics are louder than ever.

But the thesis that built Strategy — the idea that Bitcoin is the best long-term monetary asset ever created — remains unchanged. The company is still profitable on its BTC stack, still outperforming mega-cap tech over every multi-year timeframe, and still buying aggressively.

This is not a collapse.

It’s a storm.

And storms don’t break granite — they reveal it.

Written with the assistance of AI for speed, accuracy, and clarity.