In the world of investment, there is one a few almost full-proof investments you can make. One of these investments is buying a professional sports team. From people like Mark Cuban buying the Mavericks for 285 million dollars, and now the team is worth around 2 billion dollars, almost every sports team owner in America has made back on their investment.

But there is one sports team when it comes to value that has been dominating this category, and that is the Dallas Cowboys. It is hard to believe that this multiple-billion-dollar franchise was being sold for only 50 million dollars once upon a time, and it is hard to believe that Donald Trump had the opportunity to buy the team.

(Herschel Walker running back for the New Jersey Generals 1983-1985)

The Story

In 1984, Dallas Cowboys owner Clint Murchison Jr. was looking to sell the team for 50 million dollars. In 2021, this would be the equivalent of $130 million. While many other businessmen at the time were interested in buying the franchise, none were more famous than Donald Trump. During the 1980s, Trump was in the search of owning a professional football team.

Before we go on, it is essential to know that this was not Trump’s first time trying to buy an NFL team. Only three years earlier, in 1981, he tried to buy the Baltimore Colts. At the time, team owner Robert Irsay stated that he was considering relocating the team to another city or selling it. Trump led a group that offered Irsay $50 million (equivalent to $149 million in 2021) for the franchise.

Still, the offer for the Cowboys was ultimately rejected. What is interesting in this story is that Trump denies any involvement in trying to buy the team. Former Washington Redskins coach George Allen son confirmed the participation of both his father and Trump in the attempted purchase. Even NFL Commissioner Pete Rozelle stated in 1986 that Trump had tried to purchase the Colts. Trump denied this and stated that Rozelle had attempted to woo him into buying the team. In 1983, Trump had another flirt of interest in purchasing the Colts. Still, it did not amount to much, and the Colts would have their infamous relocation to Indianapolis. 

So now we get to Donald Trump’s famous interest in buying the Dallas Cowboys, and he would deny the 50 million dollar price tag for the team. Explaining his rationale for not buying the team, Trump stated in an interview with Ira Berkow of The New York Times:

“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”.

– Donald Trump (1984)

To add more bitter irony to this statement, Trump did not believe there was much room to generate profit given the price. Five years later, businessman Jerry Jones bought the team from Bum Bright (current owner) for a 50 million price tag (around 140 million). From there, he would create a dynasty on and off the field, with the Cowboys currently worth, according to Forbes, 8 billion dollars.

USFL Team

Trump would buy the USFL team New Jersey Generals for 10 million dollars. This would be 40 million dollars cheaper than the NFL teams. The USFL would eventually fold in 1986. During his time as a USFL owner, many storylines were going on. Before the 1984 season, Trump tried to hire legendary head coach Don Shula, the coach for Miami during their undefeated season. Trump would offer a salary of $1 million yearly, and Shula would decline the offer. Instead, he would hire New York Jets head coach Walt Michaels. In their first season, they would go 14-4 with a highlight win over the eventual champions, Philadelphia Stars, twice but lose in the first round of the playoffs.

On the team, there was an up-and-coming running back named Hershel Walker. During his first season with the Generals, he rushed for 1,339 yards. In 1985, the Generals acquired Heisman Trophy-winning quarterback Doug Flutie. During their second year, they would post an 11-7 record, with Doug Flutie passing for only 2,109. On the running side of the ball, Walker would run for 2,411 yards. The next closest player is Mike Rozier, with 1,364 yards. The Generals would again go on and lose in the first round of the playoffs. 

USFL VS NFL

Before the 1986 season, Trump had become very opposed to the league playing in the spring and wanted them to play in the fall, which would directly be fighting with the NFL. Trump believed that the move to the fall would lead to the league becoming as valuable as the NFL or would result in a merger between the NFL and USFL. Although some opponents opposed this idea, the team owners voted 12-2 to move the fall.

Along with moving the league to the fall, Trump led a lawsuit against the NFL. The league decided to initiate a $1.7 billion antitrust lawsuit against the NFL, hoping they would merge. The trial took place in the United States District Court for the Southern District of New York. Trump brought in Harvey Myerson (famous for his work with Joseph McCarthy) as the lead lawyer for the USFL and Roy Cohn as a consultant. 

The court saw many shenanigans during the court and many accusations being made on both sides. At one point, the NFL legal team accused Trump of paying waiters to spy on NFL owners while they were staying at his hotels. Trump denied these accusations. Also, during the trial, Trump stated that Pete Rozelle, at The Pierre Hotel in Manhattan. Rozelle during this meeting tried to talk Trump out of playing in the fall and offered him an NFL franchise if he cooperated. However, Rozelle denied making this offer.

The Verdict

After 42 days, the jury decided to favor the USFL. Although they also stated that the USFL’s financial difficulties had not been caused by the NFL, however, they awarded the USFL damages of only $1. Which was tripled to $3 because it was from an antitrust case. That is $3 as in $ 3.00 dollars, by the way. At Myerson’s advice, the league decided not to host a 1986 season as they appealed the case. However, just six days after the trial concluded, the USFL folded. Four years later, the United States Supreme Court allowed the ruling to stand, and the NFL paid the USFL $3.76 in damages, including interest.

(1984 photo of Trump shaking hands with Herschel Walker in New York after an agreement on a 4-year contract with the New Jersey Generals USFL football team) 

Post-USFL Attempted Purchases

Even if Trump was essentially blackballed from ever owning an NFL team, it did not stop him from trying to buy one again. In 1988, Trump was discussing purchasing the New England Patriots, but the thing came from it. In 2014, after the death of the Buffalo Bills owner Ralph Wilson died, Trump would bid 1 billion dollars for the 840 million value team. However, he would lose out to Terry Pegula. The natural gas businessman and owner of the National Hockey League’s Buffalo Sabres placed a bid of $1.4 billion and would acquire the team.

The What If?

It is interesting to think about what would happen if Trump bought the Dallas Cowboys. If the Cowboys would find the same success that they found under the ownership of Jerry Jones. There is a strong argument that Trump made the right decision not to buy the Cowboys back in the 1980s. You see, the person who would buy the team would be American businessman Bum Bright, and let’s say his time as the owner was not pretty. Apart from never having a winning record, they were also bleeding a lot of money. By the time Bright sold the team in 1989, the Cowboys were losing $1 million per month, according to ESPN.com.

One thing that would likely come out of Trump buying the Cowboys would be that he would had never run for president. In a 2015 interview with Sports Illustrated, which took place during his presidential campaign, Trump would comment on not getting the Buffalo Bills, saying:

“I’m glad [I didn’t get the team] because if I bought the Buffalo Bills, I probably would not be [running for president], which is much more important.”

-Donald Trump 2015 Sport Illustrated

It is incredible that many different things might not have happened if Trump had bought any NFL teams. The January 6 insurrection to Qanon might have never been found. So many more things might have never happened if Trump had not been so much of a cheapskate.