In 1983, the then-37-year-old Trump made his first foray into the world of professional football when he purchased the New Jersey Generals of the USFL after their first season of existence. It was here where Trump would fight the first battles of his brewing war with the NFL.
It was estimated at the time that Trump paid $8-9 million for the team, or about $20-22 million in today's dollars.
Source: New York Times
According to Trump at the time, he passed on several opportunities to buy NFL clubs, but he did not believe they had good growth potential.
Source: New York Times
Trump went as far as to say, ''I feel sorry for the poor guy who is going to buy the Dallas Cowboys," calling it a no-win situation. In 1989, Jerry Jones purchased the Dallas Cowboys for $140 million. Today the franchise is estimated to be worth $4.8 billion.
In the first months of owning the team, Trump immediately went after the NFL. He first tried to hire legendary coach Don Shula away from the Miami Dolphins at a time when the NFL team was in the midst of a run of two Super Bowl appearances in three years.
According to Trump, the deal broke down when Shula asked for an apartment in Trump Tower and Trump said he couldn't part with it.
Source: Palm Beach Post
According to Shula, the deal broke down when Trump spoke about the negotiations during an interview that aired at halftime of a Dolphins game in the middle of the NFL season and it became a distraction.
Source: Palm Beach Post
According to then-Dolphins owner Joe Robbie, Trump was more interested in making headlines than building a football team.
Source: Palm Beach Post
Trump already had the great Herschel Walker on his team at running back. Not content, he also went after the NFL's best defensive player, Lawrence Taylor of the New York Giants.
According to Trump, he signed a deal with Taylor within the first three months of owning the Generals, but that it would not start until four or five seasons down the road, when Taylor's Giants contract expired.
From the New York Times in 1984:
''But no one knows if we signed him - actually only three people know, that's Lawrence, his agent, and me.''
Have you signed him?
Trump smiles. ''All I can tell you is, 'no comment.' ''
Trump appeared to have his sights set on a USFL-NFL merger right from the beginning. After all, NFL teams were worth 4-5 times as much as he paid for his USFL club. A merger would have increased the value of his investment many-fold.
Early on, Trump already had thoughts of moving the USFL's season to the fall and winter to challenge the NFL head-to-head, saying, "If God wanted football in the spring, he wouldn't have created baseball."
Source: New York Times
The ultimate goal for the USFL was forcing a merger, as the AFL had accomplished. They planned a move to the fall in 1986 and filed a $1.32 billion antitrust lawsuit against the NFL. The USFL won but was awarded only $1 in damages.
With treble and interest, it was increased to $3.76. Soon thereafter, the league folded and the NFL had its first major victory over Trump.
Trump was widely blamed for the collapse of the USFL as he appeared to care more about getting into the NFL than success in his own league. In the end, he never got the merger that he had desired.
Source: ESPN
In 2014, Trump had second-thoughts about owning an NFL franchise and competed with the Pegula family and Jon Bon Jovi to purchase the Buffalo Bills.
At the time, the Bills had an estimated value of $870 million and the average NFL team was said to be worth $1.1 billion. Trump said he was going to "give it a heavy shot."
During the bidding, Trump reportedly secretly backed a local grass-roots campaign to smear Bon Jovi and instill fear in local fans that the rocker would move the team to Toronto.
The group's antics included "Bon Jovi-Free Zones" in local bars and a "Ban Bon Jovi" movement to rid the area of his group's music.
While the group did receive widespread attention, including a New York magazine article titled, "Jon Bon Jovi Is the Most Hated Man in Buffalo," the benefit to Trump's efforts to buy the team is not clear. The trust of the late owner Ralph Wilson was expected to accept the highest bid regardless of where the new owner wanted the team to play.
Read more: Report says Trump backed a bizarre grassroots campaign to smear Jon Bon Jovi
Terry and Kim Pegula ultimately bought the team for a then-record $1.4 billion. It was believed at the time that Trump's bid was just $1.0-1.1 billion.
This was Trump's second failed attempt to join the exclusive NFL club and some think this started his current vendetta against the league.
Jacksonville Jaguars owner Shahid Khan, described Trump's recent attacks on the NFL as a "personal issue" and said the president is "jealous" of the NFL.
Source: USA Today
According to NFL insider Adam Schefter, many in the NFL believe Trump specifically blames NFL commissioner Roger Goodell for his failure in buying an NFL team.
"I can tell you that there are other owners who believe that part of the reason that Trump is gone after the NFL as aggressively as he has is because he believes Roger Goodell had a hand in preventing him from buying the Buffalo Bills back when they were for sale. And because he has not been included in that ownership fraternity, he is now waging his own little vendetta against the NFL." — Adam Schefter of ESPN.
Trump's ill feelings toward Goodell came out during the infamous "Deflategate" scandal in which Tom Brady and the New England Patriots were accused of deflating footballs, an accusation that ultimately ended up in the courts and with a 4-game suspension for Brady.
Trump scolded his good friend, Patriots owner Robert Kraft, for believing that he had a deal in place with Goodell to reduce Brady's suspension if the team stopped fighting the league.
From Mark Leibovich of the New York Times:
"Bob said, 'I had a wink from the commissioner,'" Trump added, meaning that Kraft seemed to think that by standing down and not fighting the N.F.L., the league would reduce Brady’s penalty on appeal.
Kraft was under pressure, Trump explained. "He choked, just like Romney choked. He said: 'You know what? They winked at me.' I said, 'Bob when you make a deal, you should have gotten it all wrapped up.' Who ever heard of making a deal like that? Now you got this mess." Kraft should never have trusted Goodell, he said.
Trump even tried to get Brady, another friend, to sue the NFL for $500 million, offering up one of his own lawyers.
According to Trump, Brady was torn but ultimately decided against it because he just wanted to win another Super Bowl. Trump said that he told Brady he understood.
Source: New York Times
The Pigskin War began to turn in Trump's favor during the 2016 presidential election, three months before the vote, and shortly after Colin Kaepernick first sat during an anthem to protest social injustice.
Trump criticized Kaepernick's protests, saying that maybe he should find a new country.
Source: KIRO Radio
But it really took off a year later, during a rally in Alabama, when Trump upped the rhetoric and ripped NFL players for kneeling, saying NFL teams should "get that son of a b---- off the field right now, out. He's fired. He's fired!"
At the same time, Trump also criticized the NFL's recent safety measures, saying they were ruining the game: "Because you know, today if you hit too hard — 15 yards! Throw him out of the game ... They're ruining the game! They're ruining the game."
But it was the anthem controversy that Trump realized was hitting a chord with his base. He even went as far as to blame Hillary Clinton's stance — she said kneeling was not disrespecting the flag — as a big reason she lost the election.
Fox News anchor Shepard Smith called the controversy "the red meat of all red meat" for Trump's base, noting that it was easy for Trump to reframe the protests as being anti-anthem, anti-flag, and anti-military, despite the true intentions of the players.
Once that happened, the NFL was in trouble. The cause no longer mattered to many Americans, just the method.
Trump's wrath continued, calling for players to be fired and slamming the NFL for a lack of leadership and action. At one point in late 2017, Trump tweeted about the NFL 37 times in one month, accounting for 12% of his tweets during that time.
At the time, the NFL seemed content with going to war with Trump. After the increased criticism, player protests increased and became commonplace around the NFL.
An NFL spokesperson said, "Everyone should know, including the president, that this is what real locker room talk is," later adding: "If the president wants to engage in something that's productive, he has our number"
Several others in the NFL openly criticized the president including Patriots owners Robert Kraft ("I am deeply disappointed by the tone of the comments made by the president"), San Francisco 49ers CEO Jed York ("The callous and offensive comments made by the President are contradictory to what this great country stands for"), and even Goodell ("unfortunate lack of respect for the NFL").
The NFL's ticket sales were still strong in 2017, but that may be misleading as the league is driven by season-ticket sales, which happen before the season and would not have been impacted by Trump's attacks during the season. The real impact on attendance won't be known until the 2018 season.
Still, it was clear the tide was in Trump's favor, and the NFL's former punching bag was now winning. TV ratings fell for the second-straight year. DirecTV was offering refunds on the NFL package. And sponsors were threatening to pull out if kneeling players were shown during the anthems.
Sensing blood in the water, Trump upped the attacks. In October, Trump had Vice President Mike Pence leave an Indianapolis Colts game after the anthem because players were kneeling, a move that many accepted as a political stunt.
Trump's comments even started to sound less bombastic and more like somebody who knew he was winning: "The NFL is in a box, a really bad box. In my opinion, the NFL has to change or their business is going to go to hell."
While the NFL had already given up its tax-exempt status, White House press secretary Sarah Huckabee Sanders noted that tax dollars still subsidize stadiums: "If this industry is going to use money from American taxpayers to build the very fields they play on, then is it really too much to ask that they show respect for the American flag at the beginning of the game?"
Even the Super Bowl ratings were down, and there was research to suggest the protests were to blame.
Despite the NFL's attempts to work with the players on the issue, they apparently had enough. Following the season, the owners approved a new rule that would require players stand for the anthem. If they did not want to do that, they could stay in the locker room.
Some in the NFL admitted that the wrath of Trump played a factor. Dallas Cowboys owner Jerry Jones said Trump "certainly initiated some of the thinking, and was a part of the entire picture."
Source: Sports Illustrated