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Veteran trader reminds investors of the market crashes through history

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Shortly before midnight on Oct. 19, 1987, Stephen Guilfoyle finally called his fiancée.

The Wall Street veteran had been working all day on that infamous Black Monday when the Dow Jones Industrial Average — still the primary measure for U.S. stock market performance at the time — lost 22.6% in a single trading session.

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Guilfoyle’s spot on the New York Stock Exchange trading floor that day was just under the podium, where the bell is rung, right in front of Post 9, now the CNBC NYSE studio.

“NYSE trading volume for that day was three times the daily average,” Guilfoyle wrote in his TheStreet Pro column, “and at that time, we traded each and every share the old-fashioned way, priced in Spanish pieces of eight and in the old open-outcry, two-way, ongoing auction model. No circuit breakers. No time-outs.”

President Donald Trump unveiling his tariff plans.BRENDAN SMIALOWSKI/Getty Images
President Donald Trump unveiling his tariff plans.BRENDAN SMIALOWSKI/Getty Images

Worldwide losses were estimated at $1.71 trillion and the severity of the crash sparked fears of extended economic instability or even a repeat of the Great Depression.

“On a normal day, we would be done with our paperwork by sometime between 5 p.m. and 6 p.m.” Guilfoyle said. “That day, the trading floor looked like it was still open for business at 11:30 p.m., when I took my first break of the day.”

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Guilfoyle went to a bank of pay phones outside the stock exchange and called his fiancée, now his wife of many years.

“I told her that it would probably be a while until we saw each other again,” he said.

The Wall Street veteran used this blistering first-hand account to look back on the various times the market has been pummeled over the decades, dating back to 1929, as he assesses the current tariff-spawned rout.

“Since then, we’ve had the mini-crash of 1989, the dot-com bubble crash of March 2000, we had the 9/11 terrorist attacks that ultimately landed me back in the U.S. military after a long break in service, and we had the crash of 2008 that led to, or rather was a symptom of the ‘Great Recession’ or ‘Great Financial Crisis.'” Guilfoyle said.

Guilfoyle also recalled the Covid Crash of 2020, which he worked straight through, without missing a single day, despite becoming quite ill with the first variant of that virus and a horrific bout with long Covid that lasted more than two years.

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