Why Trump called buying Dallas Cowboys a 'no-win situation' in the 1980s

The NFL’s Dallas Cowboys are the world’s most valuable sports franchise in 2019 according to a report, but President Trump once considered “America’s Team” a poor investment opportunity.

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The Cowboys enter the 2019 NFL season with a $5 billion valuation, up 4 percent from last year and $400 million more than any other pro sports team in the world, according to Forbes’ latest calculations. But in 1984, Trump told the New York Times that he could have bought one of several NFL teams that were up for sale, including the Cowboys, for about $50 million.

Trump said he passed on the opportunity because NFL brands were “established and you would just see [their value] move laterally.”

''I feel sorry for the poor guy who is going to buy the Dallas Cowboys,” Trump told the newspaper at the time. “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 Cowboys later sold to a group led by businessman Bum Bright for $85 million in 1984. Instead of pursuing an NFL team, Trump bought the New Jersey Generals franchise in the fledging United States Football League. The USFL tried to directly compete with the NFL, but folded in 1985 after just three seasons of play.

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The Cowboys’ current owner, Jerry Jones, bought the team from Bright for just $150 million in 1989. The franchise has ranked as the NFL’s most valuable team for more than a decade.