Livermore, Jesse

One of the most legendary speculators in market history, Jesse Livermore made and lost several fortunes between the 1890s and 1930s. He famously shorted the market ahead of both the 1907 panic and the 1929 crash, reportedly earning $100 million in 1929 alone (roughly $1.7 billion in today's dollars). His trading principles -- cutting losses quickly, letting winners run, and reading the "tape" -- were immortalized in Edwin Lefevre's 1923 classic "Reminiscences of a Stock Operator," which remains required reading for serious traders a century later.