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A chill ripples through the global financial markets as U.S. President Donald Trump's sweeping tariff policy ignites fears of a historic stock market crash. With tensions escalating over the weekend, Wall Street investors and business leaders are sounding the alarm over what could become a new “Black Monday.”

Since Wednesday, the Dow Jones Industrial Average has shed nearly ten percent, eroding billions in market value and triggering widespread concern. As of late Sunday night, Dow futures plunged by 1,531 points—a steep 4 percent drop—pointing to what could be a harrowing start to the trading week.

The anxiety isn't confined to Wall Street. Veteran investors and billionaires, many of whom have supported Trump in the past, are now urging caution. “If Trump enforces his tariffs rigorously,” warned Jim Cramer, host of Mad Money on MSNBC, “then the 1987 scenario—the one where we were down for three days and then fell 22 percent on Monday—is the most accurate.”

Bill Ackman, founder of Pershing Square Capital Management worth over $9 billion, delicately questioned the timing of the policy. “Wouldn’t a pause be sensible,” he asked on his X-channel, suggesting the president delay the tariffs to allow companies time to adjust their supply chains. While not openly criticizing Trump, Ackman made his concern plain: without a trade deal, the tariffs could spark a “potentially severe” economic crisis.

Commerce Secretary Howard Lutnick, however, delivered a clear and uncompromising message during an interview with CBS: “There is no delay. The tariffs are coming.” He emphasized the president's commitment to what he calls a necessary re-regulation of global trade despite the tremors already being felt across the financial system.

Even Trump’s political allies are expressing concern. Texas Senator Ted Cruz, a vocal supporter during the 2020 campaign, warned of “terrible” consequences for the U.S. economy should the dispute escalate into a full-blown trade war. Elon Musk, CEO of Tesla and one of the wealthiest men in the world, added his voice to the chorus, blasting White House trade advisor Peter Navarro and calling instead for a transatlantic free trade zone with the European Union.

While Trump himself remained characteristically defiant, sharing a cryptic video on Truth Social portraying the tariff strategy as a “secret game” that is somehow working, the markets are unconvinced. Investors are jittery, deeply skeptical of a quick diplomatic solution, and bracing for a turbulent Monday that could echo the darkest moments 1987.

With no sign of a policy reversal and futures already bleeding red, the markets may now be at the mercy of a political gamble whose economic stakes are only beginning to unfold.