Jesse Livermore shorted the 1929 market crash and made $100 million.One of the first famous short-sellers in the history of the the U.S. stock market, Jesse Livermore first shorted stocks on a hunch that preceded the San Francisco earthquake. Though he really couldn't have foreseen the quake itself, the trade bagged him $250,000, and gave him a taste for short-selling. He then shorted the 1907 market crash and made $1 million. Then he made $3 million shorting wheat in 1925.But he joined the big …