The Staggering Fortunes and Falls of a Trading Legend – Jessie Livermore
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The Staggering Fortunes and Falls of a Trading Legend – Jessie Livermore

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Azeez Mustapha

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Jessie Livermore’s trading career remains one of Wall Street’s most extraordinary stories. His journey reveals both unparalleled brilliance and devastating losses, offering timeless lessons for traders today.

To understand his financial prowess, we’ve refined a widely circulated table that tracks his net worth. By consolidating annual highs and lows—adjusted for inflation—we expose the breathtaking volatility of his fortunes. These figures dwarf the market caps of many modern ASX-listed companies.

How Rich Was Jessie Livermore? The Staggering Fortunes and Falls of a Trading Legend Jessie Livermore’s Meteoric Rise

By 1908, at the age of just 30, Livermore had amassed $156 million. Remarkably, he achieved this without institutional backing, relying solely on his market intuition. His 1907 profits—$90 million—were achieved during a financial panic, demonstrating his ability to profit from chaos.

Brutal Drawdowns and Resilience of Jessie Livermore

Yet his career was far from smooth. Even before turning 25 in 1901, he faced a loss worth more than $16,000 in 2021 dollars, a minor setback compared to later disasters. By 1914, he faced a $28 million drawdown, and in 1934, a catastrophic $104 million loss. But Livermore always rebounded.

His 1917 earnings hit $115 million, and in 1929—amid history’s worst crash—he netted a staggering $493 million. These swings highlight his genius and self-destructive tendencies in equal measure.

The Staggering Fortunes and Falls of a Trading Legend – Jessie Livermore

Wealth in Modern Context

Even his “modest” years were extraordinary. His 1915 profit ($4 million) and 1937’s $15 million would rank him among today’s top investors. His 1929 fortune alone surpasses many mid-cap ASX companies.

The Ultimate Lesson

Livermore’s legacy underscores trading’s psychological demands. Talent alone isn’t enough—discipline is paramount. His story warns that even the greatest minds can be undone by their flaws.

For traders, his life remains the ultimate case study in market mastery and human vulnerability.

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