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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