President Donald Trump has made a ton of great business decisions over the years. He is a great and successful business man for a reason, and has parlayed that success to becoming the President of the United States. But, there is one decision that he could regret big time and that is passing on the Dallas Cowboys. And old quotes are resurfacing about him saying he felt "sorry for the poor guy who is going to buy" the Cowboys back in 1984 for $50 million dollars after Trump himself passed on the opportunity.
Donald Trump passed on buying the Cowboys in 1984 for $50M saying he felt “sorry for the poor guy who is going to buy” the team.
— Darren Rovell (@darrenrovell) August 14, 2025
Today, @Sportico says the Cowboys are worth $12.8 BILLION, meaning if Trump bought the team then, it would have returned 14% a year for 41 1/2 years! pic.twitter.com/F4FpZDWahT
Well, the newest list of the most expensive franchises came out and the Dallas Cowboys are the most expensive team on the list worth $12.8 billion dollars. Trump opted in to buy the New Jersey Generals of the USFL instead, and the league folded just two years later.