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The Story of Money: The trader who made $100mn from the 1929 crash — only to lose it all

Aug 4, 2026 · 56m

Summary

Hosted by Robin Wigglesworth with guest Robert Armstrong, this episode of The Story of Money profiles legendary trader Jesse Livermore. It details his rise from a bucket-shop boy to a Wall Street titan who profited $100 million by shorting the 1929 crash. The discussion covers his trading philosophy, his influence on Jay Gatsby, and his tragic loss of fortune.

Topics discussed

Introduction to The Story of Money and Jesse Livermore Reminiscences of a Stock Operator and Livermore's early life Bucket shops, board boys, and learning to read the tape Failure on Wall Street and the lesson that the market is always right Trading fundamentals, credit conditions, and market manipulation The Panic of 1907 and J.P. Morgan's intervention The Roaring Twenties: Wealth, lifestyle, and personal struggles Shorting the Great Crash of 1929 and making $100 million Bankruptcy, divorce, and the tragic end of Jesse Livermore Legacy, modern parallels, and concluding thoughts
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