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Jesse Livermore: A Journey through Triumphs and Tragedy – Detailed Timeline

Jesse Livermore was an American stock trader who is considered one of the greatest traders of all time.

Jesse Livermore is born in West Acton, Massachusetts.

Begins work in Paine Weber & Co’s Boston stockbroking offices, transferring prices from ticker-tape to quotation board.

– Makes a $3.12 profit on his first trade in Burlington stock.
– Livermore earns his initial $1,000 through trading stocks and commodities within bucket shops.


Paine Weber & Co gives Jesse Livermore an ultimatum: stop speculating in bucket shops or resign from his job. He chooses to resign.

Livermore accumulates $10,000 through trading stocks and commodities within bucket shops.


Livermore moves to NY, trades on NYSE with stockbrokers, but his fortune shrinks to $2,500 due to inconsistent success.

Livermore loses all funds through unsuccessful NYSE trading, blaming slow execution. He borrows $500, trades in St. Louis bucket shops, returns with $2,500, repays loan, and resumes trading in both markets (the Exchange and in bucket shops).


Livermore begins the day with $50,000 in his fortune, but by the end of an intense day of trading, he is left with nothing.

Livermore goes back to bucket shops and wire houses, aiming to gather funds for trading on the Stock Exchange once again. Dealing with amounts in tens and hundreds of dollars, he achieves consistent wins.

Following a year of profitable trading with the wire houses, Livermore amasses sufficient wealth to purchase a car and embrace a lavish lifestyle. Returning to New York for the third time, he carries a substantial sum of money with him.


Makes a profit of $250,000 shorting stocks on a hunch that preceded the San Francisco earthquake.

Livermore shorts the market during a crash and makes his first $1 million.

Buys a yacht then loses $200,000 trading cotton. Livermore violates his own trading rules by seeking guidance from Percy Thomas, a commodities expert, leading to negative consequences. Furthermore, he repeats this mistake by enlarging his losing position in cotton and selling his profitable position in wheat. Goes broke.


Leaves New York and goes to Chicago where a trading house, aware of his ability, offers him limited finance for trading.

Livermore is called back to New York by Dan Williamson, the trading house owner, who provides him with $25,000 to resume trading. After three weeks, Livermore earns a $112,000 profit. However, Williamson’s interference in his trading leads to losses, prompting Livermore to walk away from the partnership.


In several years of a flat market, with “no money to be made,” Livermore’s debts have grown to well over $1 million. He declares bankruptcy.

Livermore seeks assistance from Dan Williamson, who grants him the limited opportunity to trade 500 shares. Taking six weeks to carefully analyze the market, Livermore waits until he is fully confident in a profitable trade. He purchases Bethlehem Steel at a high margin of $98, anticipating its ascent due to World War I demand. As the stock rises as anticipated, Livermore acquires more shares at $115 and sells them the next day at $145. He successfully accomplishes his objective, acquiring a substantial stake once again.

After several months of successful trading, Livermore’s balance stands at $145,000.

Livermore demonstrates flawless market timing, going long during a bullish market and then shifting to short as it turns bearish. This earns him a substantial profit of $3 million. He goes to Palm Beach for the winter.

Livermore achieves an additional profit of $1.5 million, enabling him to settle all his debts from 1914. Concerned about potential future market losses, he invests $800,000 in annuities, guaranteeing a stable income for his family in case of financial setbacks. Furthermore, he establishes trusts for his wife and son, ensuring their financial security.


Livermore gives interviews to Edwin Lefèvre, resulting in a collection of newspaper articles. These articles are later compiled into the book “Reminiscences of a Stock Operator.”

In the “1925 wheat market”, Livermore seizes the opportunity to acquire large quantities of grain as prices surge, only to swiftly switch to a bearish position at the market’s peak. Taking advantage of this shift, he shorts 50 million bushels, reaping a substantial profit of $10 million.

Livermore experiences his most remarkable trading achievement by taking a short position during the significant crash of 1929. This bold move makes him profit of approximately $100 million.

Jesse Livermore is bankrupt. He has lost his entire trading fortune. The specific details of how this occurred remain unknown.


Jesse Livermore writes How to Trade in Stocks – a book for people wishing to learn stock trading.

Jesse Livermore tragically ends his life using a revolver, taking a fatal bullet to his brain. Battling with depression, his suicide note describes his life as a “failure.”

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