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October 19, 1987, was such a nightmarish day for the stock market that we still refer to it in hushed tones as Black Monday, even though a whole lot of seriously grimmer Mondays have occurred in the 35-ish years since (see American History, 2000 to present). It is still far and away the worst single day in market history, worse than any trading session in the Depression, the Covid pandemic or the financial crisis. It’s hard to imagine such a day happening again, barring a flash crash, EMT attack or UFO invasion.