Following last week’s unprecedented two-day bloodbath in stocks post-tariffs, investors are extremely nervous going into Monday’s opening of trading. Some see signs of a 1987 Black Monday type event, while others see the easy trade as higher on hopes that President Trump will announce a delay in reciprocal tariffs or some “grand deal.”

Famed market commentator Jim Cramer said on CNBC’s Mad Money Friday evening that if Trump “doesn’t try to reach out and reward these countries and companies that play by the rules then the 1987 scenario… The one where we went down three days and then down 22% on Monday has the most cogency.”

Cramer followed up on X, saying that while he doesn’t want a 1987-style crash to take place, the pattern is eerily similar. “Look I don’t want a repeat of ’87 of course,” Cramer said. “But I traded during that period and remember each day well.. We knew to sell.. and we are proud we did. But we felt like idiots because the week BEFORE the crash was so bad and we were late to sell.”

The market watcher later added that stock market circuit breakers could slow things down, unlike in 1987.

On the other side of the Monday scenario, renowned hedge fund manager Bill Ackman said with Trump’s phone likely ringing off the hook and little time to make deals before the April 9 deadline he would “not be surprised to wake up Monday with an announcement from the President that he was postponing the implementation of the tariffs to give him time to make deals.” The hedge fund manager added that Trump has “gotten the world’s attention.”

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Former JP Morgan chief strategist Marko Kolanovic thinks the risk is being short ahead of Monday.

“Trump now convinced everyone that he is crazy, and ready for global recession, Kolanovic said. “A bluff and next comes “deal” making. He will get heat over the weekend. As opposed to last week (which I posted), risk is now to go short into weekend.”

Given that the market is in the hands of Trump, who can change his mind at any moment, the former strategist said, “[n]ear term upside squeeze risk is bigger than downside risk.”

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