President Donald Trump's wealth has increased in recent years, with a big gain thanks to his stake in Trump Media & Technology Group (NASDAQ:DJT) and his family's cryptocurrency ventures. Things may have been different if Trump acquired an NFL team in 1980 with his wealth likely worth significantly more and his political ambitions possibly non-existent.
Trump Passes On Dallas Cowboys
The valuation of NFL teams has risen in recent years, with multiple teams worth more than $10 billion. The most valuable team among them is the Dallas Cowboys. Forbes values the Cowboys at $13 billion, with Sportico valuing the team at $12.8 billion.
Both media outlets report the Cowboys gaining more than 20% in value in the last year. The Cowboys have topped the Sportico NFL team valuations in each of the six years of publishing, while the Cowboys have topped the Forbes NFL rankings for 19 straight years.
Now one of the NFL's most popular teams and the most valuable, the Cowboys were once almost owned by Trump, who passed on buying the team for $50 million in 1984.
"I feel sorry for the poor guy who is going to buy the Dallas Cowboys. 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," Trump told the New York Times at the time.
Trump instead opted to buy a team in the newly formed USFL at the time (more on that below).
The average NFL franchise is worth $7.1 billion according to Forbes and Sportico with each franchise worth at least $5 billion. NFL teams collected $460 million in revenue from the league as a split from media, sponsorships, licensing and tickets. This amount makes it hard for teams not to be profitable.
The Cowboys generated $1.2 billion in revenue and $629 million in operating income, leading the NFL in both categories.
A report from The Dallas News says the valuation of the Cowboys has outgained the S&P 500 by more than double since 1996, showing the soaring value of NFL teams and how Trump may have passed up one of the most significant investment opportunities of all time.
Forbes estimates Trump’s wealth at $6 billion, significantly lower than what it could have been if he bought the Cowboys.
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"America's Team"
The Cowboys coined the term "America's Team" in 1978 after a highlight reel, arguing that the team’s frequent television appearances deserved the nickname. The team is the winner of five Super Bowls and has appeared in the modern NFL championship game eight times.
The team won Super Bowls for the 1971 and 1977 seasons, while also appearing in the Super Bowl for the 1970, 1975 and 1978 seasons. At the time, Trump could have bought the team; they were struggling, but were also one of the most well-known teams and often played in primetime or nationally televised games.
Bum Bright bought the Cowboys with a group of 11 partners for $85 million in 1984. He would keep his ownership for five years before selling the team and stadium for $140 million in 1989, netting a profit as the "poor guy" who bought the Cowboys instead of Trump.
The new owner of the Cowboys was Jerry Jones, who owns the team today.
Already former Super Bowl champions, the Cowboys may have had their greatest run of success under Jones, who made a controversial move at the beginning of his tenure by replacing legendary head coach Tom Landry.
The Cowboys won the Super Bowl for the 1992, 1993 and 1995 seasons and were one of the most dominant teams in the 1990s.
Jones' journey of betting big on oil and winning to secure the money to buy the Cowboys and his success in the 1990s is an eight-part docuseries titled "America's Team: The Gambler and His Cowboys" on Netflix (NASDAQ:NFLX).
The series ranked in the top 10 for U.S. subscribers during its first week of availability.
Fast forward to now, and while the Cowboys are still known as "America's Team" and the most valuable, they have struggled in recent years. The team has made the playoffs in only six seasons since 2010 and has a total of three playoff wins during that stretch.
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Trump's History With USFL and Professional Sports
Trump bought the New Jersey Generals for $9 million in 1983. He believed the USFL offered a better return than buying an NFL team at the time. The USFL lasted from 1983 to 1985 and some placed blame on Trump for the league's downfall. The collapse of the USFL is told in a "30 for 30" documentary from ESPN called "Small Potatoes: Who Killed the USFL."
”I’ve always enjoyed sports, starting from the time I was a kid,” Trump said when he bought the Generals. ”I was always the captain of the teams in high school. I liked baseball, golf, tennis, football, all the sports.”
Trump pushed for the league, which played games in the spring, to move games to the fall to compete directly with the NFL. He also pushed for an antitrust lawsuit from the USFL against the NFL.
The Cowboys aren't the only professional sports team he once tried to buy. He also explored bids for the NFL's Baltimore Colts (now the Indianapolis Colts), Buffalo Bills and New England Patriots. In 1983, he attempted to purchase MLB's Cleveland Indians (now the Cleveland Guardians), but wouldn't commit to keeping the team in Cleveland.
An interesting story is a connection the USFL had to Trump almost owning an NFL team. The Buffalo Bills were significantly impacted by the USFL’s competition for players in a small market. After the USFL ended, the Bills were able to sign several players from the USFL and their future coach, Marv Levy.
The moves led to the Bills becoming a top NFL franchise with several Super Bowl appearances in the 1990s.
When Bills owner Ralph Wilson passed away in 2014, Trump tried to buy the Bills team. Due to his past work with the USFL, Trump's bid was rejected and instead Terry Pegula was able to acquire the team.
The failure to acquire an NFL team was part of a decision by Trump to pursue running for the President of the United States instead.
In recent years, Trump has called for a boycott of the NFL over players kneeling during the national anthem and called for the Washington Commanders to change their name back to the Washington Redskins. In 2025, Trump became the first sitting president to attend a Super Bowl.
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Photo: Joshua Sukoff from Shutterstock
