| Year | Age | Event |
| July 26, 1877 | 0 | Jesse Livermore is born in West Acton, Massachusetts. |
| 1891 | 14 | Begins work in Paine Weber & Co's Boston stockbroking offices, transferring prices from ticker-tape to quotation board. |
| 15 | Makes a $3.12 profit on this first trade - in Burlington stock. | |
| 15 | Accumulates his first $1,000 by trading stocks and commodities inbucket shops. | |
| 1893 | 16 | Paine Weber & Co instruct Jesse Livermore that he must either quit speculating in bucket shops or quit his job. He quits the job. |
| 20 | Accumulates his first $10,000 by trading in bucket shops. | |
| 21 | Moves to New York to trade on the NYSE through legitimate stockbrokers. His fortune has been reduced to $2,500 - Livermore's trading is not always successful. | |
| 22 | Loses all funds via unsuccessful trading on NYSE - he attributes this to slow execution of his trades. Borrows $500 and goes to St. Louis to trade in bucket shops. He returns to New York with $2,500, repays the $500 loan and resumes trading on both the Exchange and in bucket shops. | |
| 22 | According to Livermore: "I was not quite twenty-three, all alone in New York with easy money in my pockets and the belief in my heart that I was beginning to understand the new machine. I was making allowances for the actual execution of my orders on the floor of the Exchange, and moving more cautiously. But I was still sticking to the tape - that is, I was still ignoring general principles; and as long as I did that I could not spot the exact trouble with my game." | |
| May 9, 1901 | 23 | At the beginning of the day, Livermore's fortune stands at$50,000. At the end of a frantic day's trading, Livermore is broke. "The ticker beat me by lagging so far behind the market. The divergence between the printed and the actual prices undid me." |
| 1901 | 24 | Livermore returns to the bucket shops and wire houses. He intends gettings a stake together to trade the Stock Exchange again. He is back to dealing in sums of tens and hundreds of dollars. He wins consistently. The wire houses try to swindle Livermore and he responds with several sting operations in which he manipulates prices of thinly traded stocks on the NYSE in order to take large amounts from the wire houses. |
| 1902 | 24 | After a year of successfully trading the wire houses, Livermore has accumulated enough money to buy an automobile and take on an expensive lifestyle. He returns to New York for the third time with a "fair sized roll." |
| Spring 1906 | 28 | Makes a profit of $250,000 shorting stocks on a hunch that preceded the San Francisco earthquake. |
| Summer 1906 | 29 | Loses $40,000 acting on a tip from Ed Harding. |
| October 24, 1907 | 30 | Livermore shorts the market during a crash and makes his first $1 million. |
| Late 1907 | 30 | Buys a yacht then loses $200,000 trading cotton. |
| 1908 | 30 / 31 | Livermore breaks his own trading rules - he takes advice from commodities expert Percy Thomas. Things go badly. Breaks his own trading rules again - increases his losing position in cotton and sells his winning 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 then summoned back to New York by Dan Williamson, owner of a Stock Exchange trading house. Williamson gives Livermore $25,000 to resume trading. After three weeks trading, Livermore has made a profit of $112,000. Williamson interferes with his trading, buying and selling on Livermore's behalf, and runs up losses. Livermore walks away from the relationship. |
| 1914 | 36 | 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. Of this, he later said, "My mind now being free to take up trading with some prospect of success, the next step was to get another stake." |
| February 1915 | 37 | Livermore asks Dan Williamson for help. Williamson offers Livermore the (very small) facility to trade 500 shares. Livermore reads the tape for six weeks before making a trade - he needs to be 100 percent sure the trade will be profitable. Livermore buys Bethlehem Steel on high margin at $98. Steel is rising because of demand from World War I. The price moves upward as he expects and, as the stock rises, he buys more at $115. The following day he sells at $145. He has achieved what he set out to achieve - he has a sizeable stake again. |
| Late 1915 | 38 | After several months of successful trading, Livermore's balance stands at $145,000. |
| 1916 | 38 / 39 | Livermore plays the market perfectly - he is long when the market is strongly bullish and then goes short when it turns bearish. He makes $3 million profit and goes to Palm Beach for the winter. |
| 1917 | 40 | Livermore makes another $1.5 million profit and pays back all his debts from 1914. He buys $800,000 dollars worth of annuities (annuities explained) to ensure his family has a secure income should he ever be wiped out in the markets again. He also puts money into trusts for his wife and son. |
| 1922 | 44 / 45 | Gives interviews to Edwin Lefèvre for a series of newspaper articles. The articles are then compiled into a book - Reminiscences of a Stock Operator - now regarded as a classic. |
| 1923 | 46 | Moves to custom-designed offices in the Hecksher Building, Fifth Avenue. Livermore wishes to be further removed from Wall Street gossip and to enjoy more secrecy for his trading operations. |
| 1925 | 48 | In the 1925 wheat market Livermore buys grain in 5 million bushel lots while the market is rising, turns bear at the top and sells 50 million bushels short for a profit of $10 million. |
| 1929 | 52 | Jesse Livermore's greatest moment as a trader. He goes short in the great crash of 1929 and makes a profit of around $100 million. |
| 1933 | 56 | The police are called when Jesse Livermore apparently goes missing. One day after disappearing he returns home, walking unsteadily. He says he spent the night in a hotel and awoke with a blank mind. Reading newspaper headlines about his disappearance brought him to his senses. His doctor's verdict: "Amnesia nervous breakdown." |
| 1934 | 56 | Jesse Livermore is bankrupt. He has lost his entire trading fortune. How he did this is unknown. He is not destitute - his family annuities save the day. He and his wife sail to Europe. "I hope to relieve my mind of some of my troubles." |
| 1939 | 62 | Jesse Livermore writes How to Trade in Stocks - a book for people wishing to learn stock trading. |
| 1940 | 62 | How to Trade in Stocks is published. |
| November 28, 1940 | 63 | Jesse Livermore dies by his own hand, via a revolver bullet through the brain. He had been suffering from depression and in his suicide note he describes his life as a "failure". |
