There was a time when buying the Dallas Cowboys was seen as more risk than reward.
Long before they became the most valuable franchise in sports, the team was struggling both on and off the field, with uncertainty surrounding its future.
And at that moment, one prominent voice believed ownership would be a losing proposition no matter the outcome.
As highlighted via CBS Sports in a 2018 article, Donald Trump offered a blunt take on the franchise’s outlook at the time.
“I feel sorry for the poor guy who is going to buy the Dallas Cowboys,” Trump said. “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.”
The story dates back to 1984, five years before Jerry Jones purchased the Cowboys and made it a money-making machine.
At the time, Trump could have purchased the now-most valuable NFL franchise for just $50 million. Instead, Trump criticized the team while making a costly mistake.
The perception around the Cowboys could not be more different today. What was once viewed as a risky investment has turned into the gold standard of sports business, with the franchise now valued at roughly $13 billion and holding that top spot globally for nearly two decades.
That transformation began when Jerry Jones purchased the team for around $140 million in 1989, a move that at the time carried significant financial risk.
Since then, the Cowboys’ value has skyrocketed by over 8,000%, driven less by championships and more by a revolutionary business model that reshaped how NFL teams operate.
Much of that growth stems from their ability to generate massive local revenue. The Cowboys consistently bring in over $1 billion annually, far surpassing other NFL franchises.
AT&T Stadium has also played a central role in that rise. More than just a football venue, it functions as a year-round revenue engine, hosting concerts, major sporting events, and entertainment spectacles.
Despite not winning a Super Bowl in decades, the Cowboys continue to dominate TV ratings, sponsorships, and global visibility, reinforcing their identity as “America’s Team.”
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