Missing Out On Buying the $6.5 Billion Dallas Cowboys Could Be Donald Trump’s Biggest Financial Regret

Donald Trump has made many questionable investments over his career. Yet, he remains quite accomplished as a businessperson if his $2.5 billion net worth is to be believed. However, one investment opportunity pops out from back in the 1984. The Former president had the chance to buy America’s Team, The Dallas Cowboys for just $5o million. But alas, the serial golfer missed out on a golden opportunity.

Trump discussed his decision in an interview with the New York Times. The former President had two investment options. He could buy NFL’s Dallas Cowboys for $50 million or go for a team in another league. Which is where he went. Yes, the Real Estate Mogul bought the New Jersey Generals of the United States Football League (USFL) back in 1984.

Short-sighted Donald Trump?

Saving $40 million in the process, as the asking price for the Generals was just $10 million. Confident in the choice, he told NYT, “I feel sorry for the poor guy who is going to buy the Dallas Cowboys,”  The former White House Resident added, “It’s a no-win situation for him, because if he wins, well, so what, they’ve won through the years, and if he loses, which seems likely because they’re having troubles, he’ll be known to the world as a loser.”

Known for his candid words, Trump certainly misjudged that investment. The NFL and Dallas Cowboys would go on to grow even bigger in popularity and net worth. In August 2021, Forbes calculated the Dallas Cowboys to be worth $6.5 Billion. That is more than any other sporting franchise in the world. And the New Jersey Generals? Well…

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Later on, Donald Trump’s good friend Jerry Jones would buy the Dallas Cowboys and that was that. During rounds of golf, the two Billionaires probably discuss the what ifs. And Trump would probably change that decision. From $50 million to $6.5 billion. That one’s gotta sting.

Jerry Jones got it done!

No one can say if the Cowboys would be worth as much if Jerry Jones was not there. It is impossible to remove him from any discussion about the team’s success. And that is not a coincidence. Jerry Jones has made the efforts to run the franchise as the main thing.

It is not just another business for Senior Jones. This is it. And even though the team has not performed excellently in over a quarter of a century, they continue to grow in net worth. Possibly owing to the entertainment value the team provides. And the ability to create household brand names out of players makes it a lucrative destination for free agents. In any case, 38 years later, the Dallas Cowboys seem better off with Jerry Jones.

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