How Rich Was Jessie Livermore?

Very is the simple answer.

Jessie Livermore’s trading career remains one of the most legendary — and cautionary — tales in trading history. To get a sense of his achievement, I have taken a table (which you can click on) that has been floating around the internet and tidied it up by removing multiple entries for a single year and posting the highest or lowest value for that year. This way, we get a sense of the enormous swings in equity he was capable of generating and absorbing. This table, adjusted for 2021 values, shows a stark and revealing portrait of a man whose trading ability allowed him to amass fortunes that dwarf the market capitalisation of many modern ASX-listed companies.

By age 30, in 1908, Livermore had accumulated the equivalent of $156 million, an extraordinary feat considering the rudimentary state of market infrastructure at the time. He achieved this not with institutional support or insider access, but through sheer talent, intuition, and an uncanny understanding of market psychology. His 1907 profits — $90 million in today’s dollars — came during a significant market panic, underlining his ability not just to survive volatility, but thrive in it.

Yet the power of this table lies not just in the eye-watering profits, but in the dramatic setbacks. By 1901, at just 24, he had already suffered a loss of over $16,000 in 2021 dollars — a minor blip compared to the $28 million drawdown in 1914 or the catastrophic $104 million loss in 1934. And yet, time and again, he recovered. In 1917, he earned $115 million; by 1929, in the teeth of the most significant financial crash in modern history, he amassed the staggering equivalent of nearly $493 million.

These swings underscore Livermore’s unique duality: unmatched genius in reading markets, paired with a near-pathological tendency toward self-destruction. His trajectory is a case study in volatility — not just in the markets, but in the human condition.

Perhaps most striking is the scale of his wealth relative to our own time. Even his more modest profitable years — 1915’s $4 million or 1937’s $15 million — would place him well within the top tier of modern Australian investors. His 1929 fortune, by itself, eclipses the current market cap of many mid-sized ASX firms. This contextualises the sheer magnitude of his impact.

His career, therefore, offers two enduring lessons. Trading is a psychological endeavour – anyone who says otherwise doesn’t understand the game. And anyone can be defeated by themselves.