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 leagues when correctly predicted the 1929 crash, and shorted the entire market, and bagged $100 million—that's serious money even now, it was an even bigger jackpot then.

Livermore's story is the basis for the fictional book Reminiscences of a Stock Operator.