Will Michael Saylor’s Strategy survive this widespread bearish market?

Michael Saylor’s Strategy is falling apart in this brutal market, and investors are running for the exits. The stock, which trades under MicroStrategy, lost 17% on Monday, sinking to $239.27—a devastating drop from its $473.83 peak in November, according to data from Google Finance.

The company has now lost nearly 50% of its value as economic uncertainty, Trump’s policies, and Bitcoin’s own struggles slam the crypto-focused firm.

Saylor turned Strategy into a Bitcoin-heavy holding company, a decision that once excited investors looking for exposure to the crypto without directly buying it.

The company’s plan to raise $42 billion through debt and stock sales to fund more Bitcoin purchases only added to the frenzy. But now, with the market turning sour, that approach is looking a lot riskier.

Bitcoin’s drop and Trump’s policies are dragging Strategy down

The sharp decline in Strategy’s stock comes as Bitcoin itself is losing momentum. The OG crypto fell by 4% on Monday, trading around $80,000, after the Trump administration confirmed that the planned Bitcoin reserve would not involve new purchases.

Instead, the government will only use the tokens it already owns, allowing only budget-neutral strategies for acquiring more.

That announcement killed the speculation that had been fueling Strategy’s rally. Investors had hoped that Trump’s return to office would mean massive government Bitcoin purchases, potentially boosting prices. Instead, they’re getting nothing.

“There’s specifics to the crypto trade, and then there’s the overall risk trade, neither of which is particularly helpful for Bitcoin,” said Steve Sosnick, chief strategist at Interactive Brokers. He added that Strategy, as a highly leveraged Bitcoin proxy, is now in even deeper trouble.

Trade wars, mass firings, and market chaos are piling on

But it’s not just crypto. The entire market is under pressure, and Trump’s trade war is making things worse. The Dow Jones Industrial Average plunged 900 points Monday, while the Nasdaq recorded its worst day since 2022 and the S&P 500 dropped 2.7%.

The uncertainty started when Trump reimposed 25% tariffs on Mexico and Canada, after briefly pausing them. That policy whiplash has spooked investors, adding to the broader fears about the economy.

Meanwhile, inside the government, Elon Musk, a key Trump adviser, is leading an effort to fire thousands of federal employees. That shake-up is only adding to the instability. Markets that once cheered Trump’s economic approach are now backtracking, as investors see more unpredictability ahead.

Trump, who once used stock market performance as a bragging point, has suddenly stopped talking about it. Instead, the White House is spinning a different story—that business leaders are still optimistic.

“We’re seeing a strong divergence between the animal spirits of the stock market and what’s actually unfolding in business,” said a White House official who spoke on the condition of anonymity, per a report from CNBC.

Jim Cramer tells investors to not be scared over Monday’s stock selloff

Some investors are no longer waiting around to see what happens. Wall Street is now bracing for a recession, and CNBC’s Jim Cramer says the market is terrified by Trump’s policy shifts.

“Of course, not many investors saw this coming—and that’s incredible to me,” Jim said Monday. “Virtually overnight, they’ve decided that we’re headed for a recession, and it’s going to happen fast.”

He compared the situation to Herbert Hoover, the president who worsened the Great Depression by raising tariffs. And he pointed to a new threat that’s freaking out tech investors: China’s DeepSeek, a startup that may have found a way to run AI technology cheaper and more efficiently than the current leaders.

Tech stocks, which had been driving market gains, are now in retreat. Investors who rushed to buy “recession-proof” stocks on Monday ended up overpaying, according to Jim. Others got burned on panic-selling.

Some traders, he said, “were ripped off on their buys”, as they scrambled to move money into safer investments. He warned against buying into the hype of recession-proof stocks too early and advised investors to focus on low-multiple techs, industrials, and banks.

As for big tech giants, the so-called “Magnificent Seven”, Jimmy declared that the group “no longer exists” in the way it once did. That’s a major change in market sentiment and another sign that investors are rethinking everything. Jim also told investors to not let Monday’s sell-off “scare you out of the market entirely.”

For now, Strategy’s fate remains directly linked to Bitcoin’s performance. If the crypto market continues to weaken, Saylor’s plan to fund future purchases with debt and stock sales could become a major liability. Investors aren’t willing to bet on Bitcoin at these levels, and that’s leaving Strategy in a vulnerable position.

Right now, nobody is stepping in to save it.