Donald Trump previously failed multiple times to buy NFL teams, engaged in a lawsuit with the league, and more recently has been at odds with it over politics and new kickoff rules. But the icy relationship appears to have thawed with President Trump announcing Monday that Washington, D.C. will host the 2027 NFL Draft.
The plan is to hold the 2027 NFL Draft on the National Mall, an iconic American location that has been the site of numerous historical events, from Martin Luther King Jr.’s “I Have a Dream” speech to the 2017 Women’s March and 2020 Black Lives Matter protests.
Trump’s plan to have D.C. host the NFL draft may have as much to do with wanting to be the man behind a massive crowd as it does repairing a historically fraught relationship with the NFL; Green Bay, the league’s smallest market, reported total attendance of 600,000 to the 2025 NFL Draft, which took place over the course of three days last month. Pittsburgh will host the 2026 draft.
NFL Commissioner Roger Goodell said during Monday’s press conference that they expect more than a million people in attendance over the three days of the 2027 draft.
This marks an about-face after years of hostilities between Trump and the NFL. In 2017, Trump was very vocal in his disdain for players who kneeled during the national anthem in support of former San Francisco 49ers quarterback Colin Kaepernick, and just recently Trump criticized the league’s new kickoff rules.
The White House declined to answer questions about Trump’s relationship with the NFL and the league didn’t immediately respond to a request for comment. But there’s no question the two sides have had a rocky relationship prior to Monday’s announcement, starting way back in 1981 with a failed effort to buy the Baltimore Colts.
Colts Owner Rejects Offer Trump Says He Never Made
Trump was at the helm of a group that offered to buy the Baltimore Colts from Robert Irsay for $50 million in 1981. Although Trump publicly denied being involved, Irsay told The Evening Sun that he turned down the offer from the Trump-led group, according to United Press International.
Keeping the Colts in the Irsay family turned out to be a shrewd financial move. Today, the franchise carries an estimated value of about $4.8 billion, or roughly 9,500% more than the $50 million takeover bid from 1981.
Trump Chooses USFL Over Cowboys, Then Sues the NFL
Two years later, a 37-year-old Trump purchased the New Jersey Generals of the United States Football League from J. Walter Duncan and Chuck Fairbanks, a deal that cost between $8 million and $10 million, according to the New York Times.
Trump chose to buy the Generals instead of paying between $40 million and $50 million to buy the Dallas Cowboys, he told the Times in 1984.
”I feel sorry for the poor guy who is going to buy the Dallas Cowboys,” Trump said in that interview. “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.”
He wasn’t necessarily wrong. The guy who bought the Cowboys in 1984, H.R. “Bum” Bright, only held the franchise for a few years before selling the team to Jerry Jones in 1989. Today, the Cowboys are worth an estimated $11 billion.
Trump’s ownership of the Generals led to his first real fight with the NFL. In 1986, Trump backed an antitrust lawsuit against the NFL that sought $1.69 billion in damages over multiple allegations, including that it had a monopoly over the TV market for football.
Ultimately, a jury found the NFL liable for one antitrust violation but cleared the league on eight other charges. In the end, the league was ordered to pay $1 in damages, and because all damage awards in antitrust suits are tripled, the NFL paid out a total of $3. Shortly thereafter, the USFL ceased operations (although it has since been revived with a 2022 relaunch).
Trump Declines to Buy Patriots Over Debt Load
In 1988, Trump was presented with the opportunity to buy the New England Patriots from Billy Sullivan, who founded the team in 1960. The team had a reported $104 million in debt, which was too much for Trump’s liking. The person who did buy the team from Sullivan, Victor Kiam, only owned the Patriots for a few years before selling to Robert Kraft in 1994.
Trump’s Past Bouts With NFL Doom Bills Bid
For 20 years, Trump stayed away from the NFL before launching a 2014 bid to buy the Buffalo Bills. The offer, reportedly worth $1 billion, was considered legitimate. As the process unfolded, however, he made public comments indicating he would not assume control of the team.
A decade later, as Trump faced a civil fraud lawsuit from New York Attorney General Letitia James, details about his Bills bid were revealed. Bankers were unsure the league would ultimately approve Trump, and there were questions about whether he had enough cash, according to the Associated Press.
In the end, Terry and Kim Pegula bought the Bills for $1.4 billion. A month later, Trump said in a social media post he was “lucky” he didn’t acquire the Bills, citing poor NFL ratings.
![Former NFL Coache Jon Gruden have a laugh while attending an NFL training camp session ten at the Miller Electric Center, Tuesday, Aug. 5, 2025, in Jacksonville, Fla. [Doug Engle/Florida Times-Union]](https://frontofficesports.com/wp-content/uploads/2026/07/USATSI_26781802_168422351_lowres-scaled-e1784132043881.jpg?quality=80&w=300)
