Carl Celian Icahn was once one of the world’s most feared corporate raiders known for daring leveraged buyouts, breaking up firms and selling their pieces. During the “roaring 1980s”, Icahn took on companies like defunct giant Trans World Airlines or TWA whose routes and other assets he sold off piecemeal and the then oil behemoth Texaco (since merged with Chevron) where he demanded asset sales, higher dividends and aggressive share buybacks.
On the evening of Nov 8, 2016, President-elect Donald Trump and his supporters were celebrating his election win at the New York Hilton in Midtown Manhattan. As results poured in, stock market futures were in a free fall because investors were nervous about the incoming president’s policies. Among the guests crammed inside the 24,000 sqft ballroom were many of New York’s best-known billionaires including Wall Street legend Carl Icahn.
Around 2am, with the stock futures projecting a market plunge, Icahn, then 81, quietly left the party and went to his nearby penthouse and started buying call options and stocks. His bet: Trump’s tax cuts and deregulation would help spark a big market rally. That daring middle-of-the-night move earned Icahn a cool billion US dollars in profits.

