16. A league of his own

Donald Trump’s love of sports didn’t end after graduating from the New York Military Academy. In 1983, he once again got involved with the sport of football, only this time from a business standpoint: as a team owner of the New Jersey Generals and eventually, league founder of the United States Football League. It was a short-lived stint, with his strategy of moving the USFL season to fall/winter to directly go head-to-head with the more established NFL becoming unpopular.