In the mid-1980s, Donald Trump owned a football team in the United States Football League (USFL), a rival to the NFL. However, his decisions and actions ultimately led to the demise of the USFL and his own team, the New Jersey Generals. Moreover, he also missed out on a golden opportunity to buy one of the most successful and valuable sports franchises in history: Dallas Cowboys.

In 1984, the upcoming Captain America of the US, Trump, bought the New Jersey Generals for an estimated $9 million, hoping to use the publicity generated by sports to boost his other businesses. The USFL was a brand-new football league that began in 1983. It chose to schedule its games during the spring season instead of directly competing with the NFL. However, Donald Trump had larger goals in mind.

Who is “the loser” here?

In an attempt to challenge the NFL, Trump aimed to shift the USFL’s games to the fall season, prompting a merger or settlement through an antitrust lawsuit. The 1986 trial yielded a disappointing outcome.

While the NFL violated antitrust laws, the USFL received only $1 in damages (later tripled to $3). Despite appealing the verdict, the league ultimately folded after three seasons due to financial losses and insufficient support.

In a report from January 1, 1984, The New York Times stated that Trump expressed his view on buying an NFL team. ”I could have bought an N.F.L. team,” Trump believed it wasn’t worthwhile, ”There were three or four available – that still are available, including, of course, the Dallas Cowboys.”

At that time 37 YO Trump mentioned, ”I could have bought an N.F.L. club for $40 million or $50 million, but it’s established and you would just see it move laterally. Not enough to create there.”

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And, Donald Trump in 80s extended his sympathy to potential buyers of the Dallas Cowboys, ”I feel sorry for the poor guy who is going to buy the Dallas Cowboys.” He said that if the buyer encountered difficulties and failed, “he’ll be known to the world as a loser.” Little did anyone know that the entry of Jerry Jones was still to come, and the time had arrived.

Jerry Jones: Worldwide billionaire, Dallas owner

Donald Trump missed a golden opportunity when he rejected the Cowboys in 1984. He thought they were not worth the $50 million asking price. But five years later, Jerry Jones bought them for $140 million and turned them into a dynasty. Jones hired Jimmy Johnson as the coach and traded star running back Herschel Walker for many draft picks. The Cowboys won three Super Bowls in the next six seasons and became one of the most dominant teams in NFL history.

They also became the most valuable sports franchise in the world, worth a staggering $13.2 billion today, according to Forbes. Trump’s Generals, on the other hand, folded along with the USFL in 1986. Trump must have regretted his decision to pass on the Cowboys, who went from mediocrity to greatness under Jones’ leadership.

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Indeed, Captain America missed the Cowboys’ successful period from 1966 to 1973, including their first Super Bowl win in 1972 and another, six years later. However, their dominance faded in 1982, leading to a nine-year stretch with only two playoff appearances. This factor influenced Donald Trump’s loss of interest.