Sportsnaut
It appears Donald Trump’s art of the deal was passing on the Dallas Cowboys in the 1980s for $50 million — missing out on billions.
Cllct.com’s Darren Rovell shared on X a quote from The New York Times in 1984 where the president called buying the Cowboys a “no-win situation.”
“I feel sorry for the poor guy who is going to buy the Dallas Cowboys,” Trump told The Times. “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.”
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.
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
— Darren Rovell (@darrenrovell) August 14, 2025
If Trump had bought the Cowboys for $50 million, he would have made a 25,500% total return with an annual compound growth rate of 14.9% over 40-plus years.
Instead, Trump bought the USFL’s New Jersey Generals in 1983. The league ceased operations after the 1985 season and folded in 1986.
In 1988, Trump reportedly showed interest in buying the Cowboys again, but was rebuffed. Jerry Jones would purchase the franchise in 1989 for $140 million.
Trump initially showed interest in purchasing the then-Baltimore Colts in 1981 and again in 1983. He also eyed the New England Patriots in 1988 and the Buffalo Bills in 2014.
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