Wall Street is know as the place of fast money and abundant cash flows. But not everyone who ever set foot beyond the pillars at its entrance shall leave with his pockets overflowing with money. There are many smart investors that make money on the markets, but only few that earn entire fortunes in the span of a few days. We kicked off this series of Wall Street’s 10 Best Trades ever made yesterday with Jesse Livermore and the early 20th-century crashes. Today we move further down the 20th century for this incredible prediction.

2. Paul Tudor Cashing In On Black Monday

The Monday in 1987 on which the U.S. stock market crashed in a percentage drop that exceeded all others in the history of Wall Street has gone down in history as Black Monday. The bleak name given to the day characterises the market sentiment that set in as investors and traders saw their entire fortunes disappearing right in front of their own eyes as if falling down a black hole. But for one man, the news of the crash were in fact positive. Paul Trudor predicted the crash before it happened and following in the steps of Jesse Livermore, he shortened the entire market risking an enormous capital on the speculation that the market would lose its footing. When Black Monday pushed the markets to rock bottom, Tudor closed his short positions by buying back devalued stocks, reportedly making $100 million on the very day the Dow Jones Industrial Average plunged 22 percent.