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4. New Football Team Owner
As Donald Trump’s real estate business grew, so did his desire to own a football team. Trump not only saw it as an excellent business investment, he also tapped into his love for the sport he experienced while at the New York Military Academy in his youth. In 1983, Trump would buy the New Jersey Generals. The team belonged to the United States Football League, a professional football conference that directly competed with the more popular National Football League. Before the USFL infamously lost its antitrust case to the NFL, Trump snagged two huge football legends for his growing team: Heisman Trophy winner Herschel Walker and Boston College quarterback Doug Flutie.