In the 1980s, Donald Trump passed on buying the Dallas Cowboys for $50 million—calling it a bad deal. Instead, he bought the New Jersey Generals of the fledgling USFL, pushing the league into a costly head-to-head battle with the NFL.
Trump’s strategy included shifting the USFL season to the fall, poaching NFL talent, and suing the NFL for antitrust violations. The lawsuit yielded only $3 in damages, and the league folded by 1986.
Meanwhile, the Cowboys surged in value and are now worth over $10 billion—highlighting what many call one of Trump’s biggest business blunders.
