History of Money Series: Black Monday 1987 - The Worst Day in Market History episode artwork

EPISODE · Aug 8, 2026 · 28 MIN

History of Money Series: Black Monday 1987 - The Worst Day in Market History

from Creating Richer Lives

October 19, 1987. The Dow fell 22.6% in a single day. It's still the worst day in the history of the American stock market, nearly double the worst day of the 1929 crash. And here's the part almost nobody remembers: the market finished that year up. In this first episode of the History of Money series, Karl Eggerss walks through what actually happened on Black Monday. Why an expensive market, rising interest rates, and a currency fight set the stage. How a strategy called "portfolio insurance", sold to pension funds as a way to protect against losses, became the thing that turned a correction into a collapse. What the Federal Reserve did on Tuesday morning, when the real danger wasn't falling prices but a financial system that was close to seizing up entirely. And why an investor who simply did nothing that day was made whole within a couple of years. But this isn't a tidy story, and Karl doesn't tell it that way. Plenty of people were genuinely ruined in 1987, almost all of them investors who had borrowed money. The circuit breakers created afterward are still debated today. And the underlying condition that caused the crash, automated selling that feeds on itself, arguably exists in greater volume now than it did then. A look at the difference between a bad day and a bad outcome.

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