Recently, I’ve been going through some trading histories and noticed that the name Jesse Livermore is repeatedly brought up in the investment world. His story is truly worth a deeper look.

Jesse Livermore (1877–1940) was one of the most legendary traders in the early days of Wall Street. He started getting involved with the market at age 14 and worked at a brokerage called Paine Webber, where he already showed an innate sensitivity to market movements. By around 1900, he had made a name for himself in the New York Stock Exchange, earning the nickname “the great bear of Wall Street.”

His most famous “battle” was during the financial panic of 1907. While everyone else was panicking, Jesse Livermore was instead shorting the market, and in the end he earned the first million dollars of his life. But what truly made him a legend was the big crash of 1929. He anticipated the market in advance and profited by about $100 million through large-scale short-selling in this catastrophe—equivalent to roughly $1.5 billion in today’s purchasing power.

Yet his life was also quite tragic. He went through four marriages, battled alcoholism and depression, and his aggressive trading style was also widely controversial. Finally, on November 28, 1940, he chose to end his own life, leaving behind a heartbreaking line: “My life was a failure.”

Interestingly, although his ending was tragic, Jesse Livermore’s trading philosophy has continued to influence later investors. His 1923 book, *Reminiscences of a Stock Operator*, is still considered an essential classic in the trading world to this day. The principles he emphasized—trading with the trend, taking quick stop-losses, letting profits run, and controlling emotions—are still applicable even today, whether you’re trading in traditional stock markets or in the crypto market.

Many successful crypto traders actually study Jesse Livermore’s strategies and then apply these ideas to trading digital assets. His thinking framework on market timing and risk management still offers plenty of inspiration for traders in the coin world today. That’s why this century-old story continues to be discussed again and again.