John Templeton - Shorted Tech Bubble in 2000

Sir John Marks Templeton (29 November 1912 – 8 July 2008) was an American-born British investor, banker, fund manager, and philanthropist. In 1954, he entered the mutual fund market and created the Templeton Growth Fund, which averaged growth over 15% per year for 38 years. A pioneer of emerging market investing in the 1960s, Money magazine named him "arguably the greatest global stock picker of the century" in 1999. [1]

A veteran at making short bets, made his biggest and best bet ever just eight years before he died, in 2000, just before the dot-com bubble popped. He shorted a whole variety basket of internet stocks, said that it was the easiest money he'd ever made. [2]