When Crypto Goes South: Michael Saylor’s Strategy Faces Its Ultimate Trial

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Imagine if your business was built on Bitcoin, not just a side gig, but the heart and soul of your whole operation.

That’s the high-stakes gamble taken by Michael Saylor’s headline-grabbing company, Strategy.

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Now, as digital assets dive like fearless skydivers without parachutes, Strategy is staring down its toughest market test yet.

Strategy belongs in the prestigious lists?

The whole crypto rollercoaster has wiped smiles off investors’ faces, but the biggest alarm bells aren’t ringing over Bitcoin or Ethereum.

Nope, analysts say it’s Strategy that’s feeling the shocks. The firm has long thrived on cozying up inside major stock indices like the Nasdaq 100 and MSCI.

These indices are like VIP clubs that herd passive funds into buying shares en masse, that is until the party’s vibe skews from bullish to brutal.

And those index custodians are now in quiet, heated debates about whether Strategy even belongs in those prestigious lists anymore.

Why? Because experts say holding more than half your assets in digital currency apparently muddies the waters. Some gatekeepers argue Strategy doesn’t behave like a traditional business anymore but more like a publicly traded Bitcoin vault.

If that definition sticks, passive capital worth billions, hearing numbers like $2.8 billion, possibly ballooning to $9 billion if others follow suit, could get yanked out of the stock, faster than you can say “crypto crash.”

Strategy’s perpetual preferred shares are also getting crushed

The timing couldn’t be crueler. Just months ago, whispers flew about Strategy possibly scoring a coveted spot in the S&P 500.

Instead, it’s now scrambling to avoid booting from the indices it’s always called home.

From a high in November, Strategy’s stock plummeted over 60%, wiping out the premium that once made investors drool over its Bitcoin exposure.

And it’s not just the common shares catching flak, as Strategy’s perpetual preferred shares are also getting crushed.

Their new euro-denominated offering is already trading below its issue price, casting a shadow on the demand for these structured bets on the company.

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80-90% Bitcoin tumble

But here’s Michael Saylor, unfazed and probably hoarding an extra shot of espresso, doubling down on his manifesto.

Strategy was built for earthquakes, not calm seas. According to him, the company can stomach an 80-90% Bitcoin tumble without drowning.

For Saylor, this chaos is the ultimate proof that his design can survive the wildest storms.

So, strap in, because this is an epic show where index gatekeepers, billions in capital, and a Bitcoin-first business model collide in a battle for survival.

Will Strategy become a crypto casualty or a comeback legend? The million dollar question.


Disclosure:This article does not contain investment advice or recommendations. Every investment and trading move involves risk, and readers should conduct their own research when making a decision.

Kriptoworld.com accepts no liability for any errors in the articles or for any financial loss resulting from incorrect information.

András Mészáros
Written by András Mészáros
Cryptocurrency and Web3 expert, founder of Kriptoworld
LinkedIn | X (Twitter) | More articles

With years of experience covering the blockchain space, András delivers insightful reporting on DeFi, tokenization, altcoins, and crypto regulations shaping the digital economy.

📅 Published: November 22, 2025 • 🕓 Last updated: November 22, 2025
✉️ Contact: [email protected]

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