Ask some Wall Street veterans where they were on October 19, 1987 and they will likely regale you with details of any crisis. My life changed that day in ways that often creep up on me. Indeed, Black Monday was the single worst day in Wall Street history, with the Dow Jones Industrial Average plunging by more than 22 percent in one session--that’s the equivalent of the blue chip index diving by more than 5,000 points today.

It was a “First Class Catastrophe”, according to our first class guest and storyteller supreme, Diana Henriques, who dropped by the studio to help us retrace the events that led up to that day.

Diana joined us on the podcast earlier this year when her book, The Wizard of Lies: Bernie Madoff and the Death of Trust, was made into an HBO movie. This time around Diana is joining us to discuss her latest book, A First-Class Catastrophe: The Road to Black Monday, the Worst Day in Wall Street History.  As Diana recounts, Black Monday was more than seven years in the making and threatened nearly every U.S. financial institution.

There were missed opportunities, market delusions, and destructive actions that stretched from the “silver crisis” of 1980 to turf battles in Washington and a rivalry between the New York Stock Exchange and the Chicago Mercantile Exchange.

Here’s the crazy thing...you’d think that after Black Monday, lessons would be learned. But in her analysis, Henriques demonstrates how that Monday in the fall of 1987 was the predicate to the financial crisis of 2008. Sadly, investors, regulators, and bankers failed to heed the lessons of 1987, even as the same patterns resurfaced.

This was a fascinating interview for me because I lived through this period. I had just started my career on Wall Street, as the chaos was unfolding. I watched firsthand as my father nearly lost his business.  This chat was like going down memory lane and it’ll give you guys a good glimpse of the life I used to live before I started hosting podcasts and radio shows!

“Better Off” is sponsored by Betterment.

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"Better Off" theme music is by Joel Goodman, www.joelgoodman.com.

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