Open trading account 
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.
Paul Tudor Jones made an estimated $100 million when he predicted Black Monday in 1987 and shorted the stock market.
Using technical analysis and historical S&P data, Paul Tudor Jones correctly predicted that the market was going to crash in 1987, and proceeded to massively short stocks.
The Dow plunged 22%, and estimates put his gains from that trade at around $100 million.
Shortly after he did so, PBS released a documentary about Jones, titled Trader. Jones bought almost all the copies of the movie as soon as it was released—he didn't want anyone seeing it. There's some speculation that Jones hated the documentary because he felt it gave away his trade secrets. Or that he just didn't like how he looked when he was trading.
Andy Krieger shorted the Kiwi in the late 80s and made $300 million.
In 1987, just after the Black Monday crash investors dumped the U.S. dollar and rushed into other currencies. Andy Krieger, a the 32-year-old currency trader at Banker's Trust, guessed that the New Zealand dollar, also know as the 'Kiwi', was dangerously overvalued.
Using options, which were a relatively new financial instrument at the time, Krieger took up a short position against the Kiwi worth millions of dollars. So much so that his sell orders actually exceeded the New Zealand money supply. The kiwi yo-yoed between a 3 - 5 percent loss and netted Kreiger's employers about $300 million. Krieger got a $3 million bonus out of the deal.