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The Jazz Age hero

Jesse Livermore was the most successful speculator of the first half of the 20th century. His techniques and insights still have relevance today
May 17, 2013

The rise of Jesse Livermore was only slightly less shady than that of his fictional American contemporary, Jay Gatsby; yet his fall was almost as spectacular as that of F Scott Fitzgerald's Jazz Age hero. Like Gatsby, as a boy, Livermore made copious notes on how to make himself better day by day and in every way. Like Gatsby, driven by a furious ambition, he became prodigiously wealthy when still young and celebrated his wealth with fabulous parties for the rich and famous at his Long Island mansion. Like Gatsby, his life was wracked by love for a beautiful but shallow woman. And, like Gatsby, he met his death by violence - though, in Livermore's case, the gun was fired by his own hand (to be precise, in the men's room of the swanky Sherry-Netherland Hotel on Manhattan's upper east side in November 1940).

So, when we write about Jesse Livermore, we write about a man who could have inspired another 'great American novel’ from the typewriter of Fitzgerald, or Ernest Hemingway or William Faulkner. Yet, almost without exception, the one we write about is Jesse Livermore, the stocks and commodities trader; Jesse Livermore, the 'boy plunger', who, as a teenager, was banned from betting in Boston's bucket shops because he had cleaned them out; Jesse Livermore, the speculator, whose peak was at Wall Street's darkest hour, when he short sold the Wall Street Crash and, by the end of 1929, had a fortune of over $100m.

There are two things to say about that fortune. First, let's put it into a contemporary context. Inflate it by the change in US consumer prices and, in today's money values, it is worth about $1.4bn. That would make Livermore ultra wealthy, but perhaps not eye-blinkingly so. After all, Bill Gross, the best-known bonds fund manager in the US today, is worth $2.1bn, according to Forbes magazine.

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