On the night of Trump's victory.

Carl Icahn has been a vocal market bear lately, predicting doom and gloom. He's coming off one of the worst investment stretches of his storied Wall Street career, and his investment fund is headed toward its third straight year of losses after sliding 18% in the first half of 2016. But Icahn's fortunes may have begun improving following the election of Donald Trump, whose campaign he publicly supported: On the night of Trump's victory in November 2016, Icahn reportedly dumped $1 billion into stocks as world markets started panicking. By the next day, global exchanges had leveled off, and Icahn walked away with a tidy profit. Still, his portfolio continues to carry risk; he has been buying more shares of Herbalife following its Federal Trade Commission settlement in July 2016, and continues to bet on auto suppliers like Federal-Mogul. Icahn grew up in Queens and eventually got a securities arbitrage gig at Dreyfus & Co. He made billions of dollars staging buyouts in 1980s.