Jesse Livermore was a legendary figure in Wall Street history, known for making and losing several fortunes throughout his career. He is most famous for shorting the Wall Street crash of 1929, an event that reportedly netted him $100 million. This amount is estimated to be equivalent to $1.5 billion in today's money or, when scaled to the US economy, around $30 billion, making it one of the largest trading hauls in history.
Livermore's life was characterized by extreme highs and lows. He began his trading career as a teenager, rapidly accumulating wealth in "bucket shops" before moving to Wall Street. Despite his immense successes, he also faced numerous setbacks, including multiple bankruptcies. Before the 1929 crash, his fortune was estimated at $20 million, and he was known for lavish spending on yachts and parties, even inspiring F. Scott Fitzgerald's character Jay Gatsby.
His trading style involved leveraging big market swings and speculating heavily in commodities like cotton. However, he also had a pattern of making large sums, being tempted into new market areas, losing heavily, and then rebuilding his wealth. Livermore's career was significantly impacted by the changing regulatory environment, particularly the new Roosevelt stock-trading rules of the 1930s, which made it harder for operators of his type to thrive. By 1937, the market was too strictly regulated for him.
Tragically, Livermore's life ended in suicide on November 28, 1940, at the Sherry-Netherland Hotel in Manhattan. He left an eight-page suicide note to his third wife, stating he was "tired of fighting" and deemed himself a "failure." His death, while not solely attributed to financial losses, was seen as connected to his personality as a trader, seeking constant risk and excitement, leading to tremendous highs and ultimately devastating lows from which he could not recover.
