Donald Trump said buying Dallas Cowboys was a ‘no win situation’ before they became the most lucrative US franchise

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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.

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Donald Trump once called the Cowboys’ purchase a ‘no-win situation’

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.

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