THE 28TH INSTALLMENT of the Ultimate Fighting Championship was a trial run. Though 36 states had banned the UFC, the New Jersey State Athletic Control Board allowed the then-owner, Semaphore Entertainment Group, to host its first sanctioned event on Nov. 17, 2000, at the Taj Mahal in Atlantic City, a hotel and casino owned by real estate mogul Donald Trump. Fighter Randy Couture returned to the UFC for the first time since 1997 and recaptured his heavyweight championship against Kevin Randleman in the main event, but the most consequential appearance that night happened in the crowd of 5,000 fans.
Dana White attended, not as a UFC official but as the manager of fighter John Lewis. White was with friends Lorenzo Fertitta and Frank Fertitta III, brothers who were Las Vegas casino owners and trained in jiu-jitsu under Lewis. As they soaked in the atmosphere, they discussed all the things they could do when the Fertittas' company, Zuffa LLC, owned an MMA promotion.
Three months later, White returned to Atlantic City as UFC president at Trump's Taj Mahal for UFC 30.
That was a launching pad for the UFC and the beginning of a 25-year friendship between Trump and White that has led to Trump attending numerous UFC events, including four as a sitting president, and White introducing presidential candidate Trump at two Republican National Conventions.
"He is one of my very good friends," White told ESPN last month, adding that Trump is one of 10 friends in his small circle. "Like, you have a group of friends in your life that are, especially at my age, you've gone through all the s--- in your life and all this stuff. Me and this guy have been friends for 25 years and ... our relationship gets stronger every year."
On June 14, Trump's 80th birthday, their friendship will reach a new landmark when the White House hosts a UFC fight card. Presidents have invited championship teams to visit the White House, hosted amateur games on the South Lawn and played tennis or basketball there themselves. But UFC Freedom 250 is unprecedented -- a live professional sporting event staged on the White House grounds. ESPN has combed through archival content from dozens of outlets to present the many ways two careers have crossed, creating a path for UFC fighters to walk into the Octagon on the South Lawn of the White House.
• Jan. 11, 2001: Zuffa LLC purchases the UFC for $2 million and appoints White as the promotion's president. After having trouble landing a venue to host the UFC's two upcoming events, Zuffa makes a deal with Trump to host UFC 30 and UFC 31 back at the Taj Mahal in Atlantic City.
In all the years since, White has repeatedly expressed appreciation for Trump welcoming his company, saying the casino owner's involvement legitimized the UFC. "None of the venues wanted this," White told CBS's "60 Minutes" in 2025. "They didn't believe in it, they didn't like it, and they were worried about the type of crowd that would show up for this type of event."
After Trump stepped up, White remembered the time this way: "When the Trump brand was here [White holds his hand high overhead] and the UFC brand was down there [holding his hand near the floor], he saw it and said, 'I'd love to have it at my casino.'"
However, Trump's casino business faced severe financial problems at the time. According to PBS's "Frontline," his Atlantic City operation reported a net loss of $133.8 million for the 1999 fiscal year. The umbrella company holding the casinos filed for bankruptcy twice within the following decade.
• Feb. 23, 2001: The first event under Zuffa ownership, UFC 30, is at the Taj Mahal. In the main event, Tito Ortiz successfully defends his light heavyweight championship by slamming Evan Tanner unconscious in 30 seconds. White later said Trump was in attendance all night long at UFC 30 and UFC 31, also at the Taj Mahal, though ESPN could not find visual evidence of it, and the account has been disputed by multiple former UFC employees.
• June 29, 2001: The promotion's next fight card is at 20,000-seat Continental Airlines Arena, the East Rutherford home of the New Jersey Nets and Devils. For the first time, photos and the broadcast show Trump cageside. The UFC then books its next two fight cards in Las Vegas, at Mandalay Bay Events Center and at MGM Grand Garden Arena. White reflected on Trump's early support of the UFC in a 2011 interview, saying, "The guy saw this thing coming, was into it and gave us our first shot, and you'll never hear me say anything bad about Trump."
• Feb. 28, 2003: UFC 41 is held at Atlantic City's Boardwalk Hall, which has nearly three times the seating capacity of the Taj Mahal. Heavyweight Tim Sylvia and lightweight BJ Penn successfully defend their titles. Trump Plaza serves as the corporate host for the event, and the Taj Mahal casino features $5 chips with the UFC headliners' faces on them.
• Oct. 22, 2004: The UFC is back at Boardwalk Hall for UFC 50. It is headlined by Ortiz against a short-notice opponent, but the event is best known for being the card on which Georges St-Pierre first fights for a UFC title. St-Pierre loses to Matt Hughes. Also in the building is a production crew for the soon-to-debut reality TV show "The Ultimate Fighter." When TUF aired months after "The Apprentice" made Trump a reality TV darling, the show launched White to stardom, as well. A USA Today story drew a comparison, saying TUF had cast White in the "Donald Trump role."
• June 5, 2008: Trump calls a news conference at Trump Tower in Manhattan to announce a partnership with a startup MMA promotion, Affliction Entertainment, a venture of the Affliction clothing brand. The new promotion's star is heavyweight Fedor Emelianenko, widely considered the best MMA fighter in the world.
The Affliction brand had a long sponsorship history with the UFC, but when word got out that this new fight promotion was about to launch, the UFC banned its fighters from wearing Affliction clothing. At the introductory news conference, Trump acknowledges the potential competition between the UFC and Affliction by raising a topic that exists to this day in MMA: fighter pay. "If there's only one organization," he says, "you can pay the fighters five dollars and they'll be happy to fight."
However, Trump is not critical of the UFC boss. "I have great respect for Dana White," he says. "Some of the people in the room may not like him. I like him and I think he's done a very good job."
• July 19, 2008: Affliction Entertainment holds its first MMA event at the Honda Center in Anaheim, California, cheekily named "Affliction: Banned." It is headlined by Emelianenko knocking out former UFC heavyweight champion Tim Sylvia in 36 seconds. Two other former UFC heavyweight champs, Andrei Arlovski and Josh Barnett, fight on a card filled with talent signed away from the UFC. Megadeth, interrupting an international tour of summer music festivals, performs during the $39.99 pay-per-view.
Trump is asked afterward whether he thinks Affliction will take over MMA from the UFC. "I think it probably will," he says. "All the fighters want to be with us. I think it probably will take over."
That same night, the UFC holds a hastily scheduled fight card on five weeks' notice, made available on basic cable outlet Spike TV. The main event features a rare non-PPV appearance by the UFC's best fighter, Anderson Silva. White refuses to call this scheduling move counterprogramming, saying simply he is "giving the fans what they want."
• July 24, 2009: Almost exactly a year after its first MMA event, Affliction Entertainment folds. The abrupt end comes after one of the headliners on the promotion's third scheduled fight card, Josh Barnett, fails a steroid screening. Hours after the cancellation of "Affliction: Trilogy," the company announces it no longer will promote fights and instead will return as a clothing sponsor for the UFC.
This development shows White's business vision. At the UFC postfight news conference following Silva's KO win a year earlier, on the same night as Affliction's debut card, White had downplayed Affliction's chances of success, saying, "I figure after tonight those guys will be out of business." Asked why, White added, "Because they spent a lot of money tonight. And I know more about this business than they do. When you spend a lot of money and you don't get that money back, you usually go out of business."
White never mentioned Trump's name in his criticism of Affliction.
• Aug. 18, 2011: The UFC announces a seven-year, $700 million broadcast deal with Fox. White later revealed that Trump sent him a copy of a New York Times writeup about the deal with a note written on it that says, "Congratulations, Dana. I always knew you were gonna do it."
• Nov. 15, 2015: Hours after Holly Holm knocks out Ronda Rousey in a huge upset at UFC 193, Trump posts on X (then known as Twitter): "Glad to see that @RondaRousey lost her championship fight last night. Was soundly beaten - not a nice person!" Months earlier, Rousey had said she was voting for Bernie Sanders and downplayed Trump to CNN: "I don't want a reality TV star to be running my country." Rousey does not respond to Trump's "not a nice person" comment. Years later, she revealed that White asked her in 2016 not to speak badly of Trump. She said she agreed "because I owe Dana my life."
• Dec. 11, 2015: For the first time publicly, White backs Trump's presidential campaign. "Donald will get my vote," White says in an interview with TMZ.
• July 11, 2016: Steven Cheung, the UFC's director of communications and public affairs, leaves the promotion to join Trump's political campaign. Cheung had managed messaging for the UFC and its outspoken CEO since 2013. "When you're in communications, and you have a Dana White-type person, I think he would have learned a lot from that," UFC vice president of regulatory affairs Marc Ratner told NOTUS. "And that may have helped him there with the president."
• July 19, 2016: White speaks at the Republican National Convention in Cleveland, Ohio. The UFC CEO begins his address with, "What's up, GOP? ... I'm sure most of you are wondering, 'What are you doing here?'" He draws applause when he addresses why he supports Trump. "Let me tell you something: I've been in the fight business my whole life; I know fighters," White says. "Ladies and gentlemen, Donald Trump is a fighter, and I know he will fight for this country."
• Nov. 8, 2016: White and his wife, Anne, celebrate their 20th wedding anniversary in New York City and watch election night results from their hotel. When Trump is announced the winner, his son-in-law Jared Kushner calls White to invite him to Trump's victory party at the New York Hilton Midtown. White told reporters that Trump had planned to commemorate his victory at UFC 205 inside Madison Square Garden four days after getting elected. Ultimately, Trump did not attend the fights. "I don't think Donald really realized what his duties were going to be had he won," White said.
• July 11, 2017: At a prefight news conference for an upcoming Floyd Mayweather vs. Conor McGregor boxing match the UFC is promoting, White says the White House had reached out about securing tickets for the president, but ultimately Trump decided not to attend. "[Trump] feels like he'll ruin events," White says. "Secret Service is going to have to go through the place, shut down streets and create crazy traffic."
• Aug. 2, 2018: Trump hosts White and then-UFC fighter Colby Covington at the White House. In the wake of Covington's interim welterweight championship victory over Rafael dos Anjos in June, Covington and White visit the president to celebrate Covington's victory and shoot video for an upcoming UFC documentary.
• Nov. 14, 2018: UFC Fight Pass releases a mini-documentary online called "Combatant in Chief: the Story of Donald Trump's History in Combat Sports" that details White and Trump's long friendship. In a trailer for the film, which has since been removed from the UFC's channels, Trump says, "Well, there is a fighter's mentality -- whether you're in the UFC or whether or not you're president. People like Dana White have that and they have it in spades."
• Nov. 2, 2019: Trump becomes the first sitting U.S. president to attend a UFC event. As he walks out alongside White to cageside at Madison Square Garden in New York for the main card of UFC 244, headlined by Jorge Masvidal vs. Nate Diaz in the first BMF title bout, Trump is greeted by a mix of cheers and boos -- a more favorable reception than earlier in the week when Trump appeared at a World Series game in Washington to a "Lock him up!" chant from the crowd.
At the postfight news conference, White expresses no concern for the mixed reception Trump received. "This is America. You can believe and do whatever you want. If you want to boo, you can boo." he says. "... I just felt like tonight we were gonna walk in and whatever happened happened. The guy told me as a friend he would come see the fights, and he did tonight. I appreciate him, and it was a big night for the sport."
• Feb. 20, 2020: White appears at a Trump rally in Colorado Springs, Colorado, and says he and Trump have gotten closer since Trump was elected president.
• May 9, 2020: Trump congratulates White and the UFC on being the first professional sports league to resume action during the COVID-19 pandemic. "Get the sports leagues back, let's play," Trump says in a video prerecorded outside the White House's Oval Office that airs on ESPN before UFC 249. "Do the social distancing and whatever you have to do, but we need sports. We want our sports back."
• July 10, 2021: Trump attends UFC 264 at T-Mobile Arena in Las Vegas. This is his first appearance at a UFC event since the end of his first presidential run. Although Trump is in attendance, he is not shown on the broadcast. After the event, White expresses frustration with his production crew. "We were getting ready to show him right between the co-main and main events," White says in an interview with TMZ. "Let me tell you what, massive f--- up by my production team. But, you know, it's live TV and these things happen."
• Dec. 29, 2021: White appears on "The Fight with Teddy Atlas" podcast and recounts his appearance for Trump at the 2016 Republican National Convention. He reveals that his decision to appear was not popular among his associates. "Everybody, and I mean f---ing everybody, told me not to do it," White says. "I'm like, 'Are you crazy, man?' Yeah, there's no f---ing way in hell I'm not doing that for him. Then, once I spoke, you know, our friendship went to a whole 'nother level."
• April 8, 2023: After nearly two years without appearing at a UFC fight card, Trump makes an unannounced appearance at UFC 287 at Kaseya Center in Miami four days after he pleaded not guilty in New York to 34 felony counts of falsifying business records related to a cover-up of an extramarital affair. He walks to his seat flanked by White and another of his friends, musician Kid Rock, whose "American Bad Ass" plays in the arena. As he takes his cageside seat, the crowd stands, cheers and chants "U-S-A." It's the first of six UFC events he will watch in person during his second presidential campaign.
• Nov. 14, 2023: White appears on an episode of Theo Von's "This Past Weekend" podcast. White says he refused to take down a promotional video for Trump from his personal social media accounts after a "big" UFC sponsor asked him to. "Don't ever f---ing call me and tell me who to vote for," he rails.
• June 1, 2024: Two days after he is found guilty in New York on 34 felony counts, Trump is cageside for UFC 302 in Newark, New Jersey. The video of Trump and White walking to the cage while being cheered on by the Prudential Center crowd is used to announce Trump's official TikTok account. "The President is now on TikTok," White says in the video. "It's my honor," Trump responds. Trump gained more than 2 million followers in less than 24 hours after posting the video. To date, his debut post is the second-most-viewed on Trump's TikTok.
At the time, 43% of Americans under age 30 said they got their news from TikTok, according to the Pew Research Center.
• July 13, 2024: There is an assassination attempt on Trump during a presidential campaign rally outside of Butler, Pennsylvania. "I am absolutely sick to my stomach and in complete shock," White posts to social media after receiving the news.
Two days later, White appeared on "The Pat McAfee Show," praising Trump for his resilience during the shooting. "Everybody wants to act like a tough guy, right? Well, when the s--- goes down, you find out who tough guys are and who tough guys are not," White told McAfee. "This guy is the legitimate ultimate American badass of all time. A guy takes a shot at him, he goes down, he stands up and then he starts chanting to the crowd, 'Fight, fight, fight.' I literally was blown away."
• July 18, 2024: White is the final speaker at the Republican National Convention in Milwaukee, tasked with introducing the party's presidential nominee, Trump. His position at the end of the program is notable because the job is usually is reserved for the nominee's spouse or a family member. "The fact that he asked me [to introduce him], and the fact that his family also thought it should be me, is probably one of the greatest honors of all time for me," White later told Time magazine.
• Sept. 10, 2024: During a postfight interview on an episode of "Dana White's Contender Series," White says he spoke to Trump "an hour before" Trump's presidential debate vs. the Democratic nominee Kamala Harris, which Trump said he looked at "like a heavyweight fight."
"First of all, it's the second time he has to debate. He already did a debate," White says, referring to the debate held in the summer between Trump and President Joe Biden. "They didn't like how the debate turned out. They want to kick that guy [Biden] out. He's unfit to run, yet he's still the President of the United States. Now they bring in somebody who wasn't elected to actually be in there."
• Oct. 22, 2024: YouTubers the Nelk Boys post a video with Trump on a private flight. While landing in Las Vegas, Trump calls White to say, "I'm with your favorite people, the Nelk Boys ... I let them ride in the plane, Dana. I don't let too many people ride in the plane, I'll be honest with you" before calling White "the greatest of all time."
• Oct. 27, 2024: White speaks during a Trump rally at Madison Square Garden in New York City, just before election day on Nov. 5. "Ladies and gentlemen, we are nine days away from the most important election of my lifetime," White tells the crowd. "The stakes have never been higher, and the choice has never been clearer."
• Nov. 6, 2024: Hours after Trump is elected president for a second term, White addresses the crowd at an early-morning victory party at the Palm Beach Convention Center in West Palm Beach, Florida, thanking influential podcasters and streamers Adin Ross, Theo Von, the Nelk Boys and UFC commentator Joe Rogan for their part in getting Trump reelected. Each of them platformed Trump ahead of the election.
In an interview with The New Yorker two years later, White said he had been trying to connect Rogan and Trump "for probably like six years." He also said he convinced Rogan to publicly back Trump ahead of the election.
"Early on, I started telling the president, if you stay on Fox, and only Fox, you're going to lose [the election] because most of the people on Fox are already voting for you and every other network says horrible things about you," White told The New Yorker. "You gotta start getting into podcasts."
• Nov. 7, 2024 Sports Business Journal publishes a story in which White says he has no interest serving in President Trump's administration. "Donald Trump is one of my very good friends. He did a great job in his last term as president and I know he will do an even better job the next four years," White tells SBJ. "I have no personal political aspirations."
• Nov. 16, 2024: Trump is back at MSG to take in UFC 309, his first UFC event as president-elect. In the main event, Jon Jones makes his only title defense as heavyweight champion, beating two-time champ Stipe Miocic by third-round TKO. At the postfight news conference, White is asked if Trump's election changes anything for the UFC. "I think it's positive for the world, to be honest with you," he responds. " ... I think for the whole country, it feels like somebody hit the reset button."
White later indicated that this appearance was the first time Trump had mentioned the possibility of an event at the White House. "We were at an event at Madison Square Garden and the president leaned over to me and said, 'You know what? We should do an event at the White House,'" White said. "And I said, 'Yes, yes, we should do an event at the White House.'"
• Nov. 19, 2024: White swears off politics in an interview with The New Yorker, saying, "I'm never f--ing doing this again. ... It's gross. It's disgusting. I want nothing to do with politics."
• Jan. 6, 2025: Mark Zuckerberg, a UFC fan and jiu-jitsu practitioner, appoints White to the Meta board of directors. The Associated Press suggests the move could be partly motivated by a desire to curry favor with the incoming presidential administration.
• Jan. 20, 2025: At Trump's presidential inauguration ceremony, White has a prominent seat among the 600 in the Capitol Rotunda behind presidents Barack Obama and George W. Bush.
• April 12, 2025: Trump attends UFC 314 at Kaseya Center in Miami, then UFC 316 at Prudential Center in Newark, New Jersey, two months later.
• July 3, 2025: Trump makes the first public mention of a possible UFC fight card at the White House during a rally in Des Moines, Iowa, to kick off a yearlong celebration of the 250th anniversary of the United States. Trump says he wants upward of 20,000 spectators in attendance on the White House grounds for the fights on July 4, 2026. He also states his intention to host a festival at the National Mall in Washington, D.C., and an athletic competition for high school students from across the country.
"So every one of our national parks, battlefields and historic sites are going to have special events in honor of America 250," Trump says, "And I even think we're going to have a UFC fight."
Despite Trump's announcement, a White House spokesperson says there are no more details to share. White House Press Secretary Karoline Leavitt later stated that the president was "dead serious."
• Aug. 28, 2025: Two weeks after White teased a trip to Washington to visit with Trump and his daughter Ivanka, the UFC CEO confirms that event planning with the White House is underway.
"We had a meeting at the White House, [which] could not have gone better," White says in a live video on Instagram. "It's gonna be awesome. The White House fight is on. ... I will have more details on that in the next couple of weeks."
• Oct. 5, 2025: Trump says at a celebration of the U.S. Navy's 250th anniversary that the White House fight card will take place on his 80th birthday, June 14. Earlier that week, White claimed it would cost the UFC $700,000 to replace the grass on the South Lawn after the event and that weigh-ins would be held at the Lincoln Memorial.
• Dec. 7, 2025: Trump claims that "eight or nine championship fights" will take place at the White House and that the UFC is not fielding anticipated matchups on other cards in order to book them for June 14. When asked about the matchmaking, White repeatedly says the UFC will not begin arranging White House fights until after the new year.
• March 7, 2026: The UFC announces the White House fight card matchups during UFC 326 at T-Mobile Arena in Las Vegas. Unlike Trump's prediction, the official announcement features one title fight, an interim title fight and four other bouts.
• April 11, 2026: Trump attends UFC 327 at Kaseya Center in Miami. White recounts in the postfight news conference an exchange he has with Trump, a fan of heavyweight Derrick Lewis, whom he is known to call after wins.
"About an hour ago, the president leans over to me and says, 'Why is Derrick Lewis not on the White House card?"' White recalls. "And I said, 'Hold on, Mr. President.' I stepped away and called Derrick Lewis and said, 'Derrick, the president just asked why you're not on the card. Do you want to fight on the White House card?' He said, 'Of course.'"
During the fight card, Josh Hokit is victorious against Curtis Blaydes in one of the most entertaining heavyweight fights of the year. White says in the news conference that he found Hokit getting into an ambulance after the fight and rewarded him with a matchup against Lewis on the White House card.
• April 25, 2026: Trump attends the White House Correspondents' Association Dinner for the first time as a sitting president and White is "right in front of where the president was," according to the UFC CEO. The president, vice president and their spouses are rushed out of the ballroom after gunshots ring out. White recounts to reporters that guests in the ballroom were instructed to take cover but that he did not obey. Instead, he describes an "awesome" experience.
"Inside, they started up. All of a sudden, it just started getting noisy," White tells reporters. "Tables getting flipped over, guys running in with guns and they were screaming, 'Get down!' I didn't get down -- it was f---ing awesome. I literally took every minute of it in. It was a pretty crazy, unique experience."
• May 6, 2026: Trump hosts UFC fighters on the Freedom 250 fight card in the Oval Office. Lightweight champion Ilia Topuria and his challenger, interim champion Justin Gaethje, are there with Ciryl Gane and Alex Pereira, who will fight for the interim heavyweight title. During the promotional event, Trump shows renderings of the venue on the White House's South Lawn.
"As you know, [on] June 14, we're having a big fight," Trump says. "It's never gonna happen again. It's never happened before."
• May 11, 2026: White writes a letter to Trump, asking him to implore Congress to reverse a provision within the One Big Beautiful Bill Act that places a 90% limit on gambling loss deductions. "The current law makes it irrational to bet in the United States because you could end up owing taxes even when you lose or having a tax bill that exceeds your winnings for the year," White writes. "The UFC supports a healthy, legal sports betting market to drive fan engagement, broadcast value and sponsorships. When legal betting is discouraged, it hurts the ecosystem we've spent years building in partnership with state regulators and licensed operators."
• May 29, 2026: Financial disclosures for Trump's trust fund reveal that it acquired stock in TKO Group Holdings, the parent company of UFC and WWE, on March 25, weeks after White announced the Freedom 250 fights. While the exact figure is unknown, between $15,001 and $50,000 worth of TKO stock is disclosed.
• June 1, 2026: Trump tells Fox News that "you'll never see it again" in reference to the White House hosting Freedom 250 and that he's anticipating high viewership ratings. "Dana is an amazing man," Trump says. "He's done an amazing job, he's put together something that -- this will be the highest-rated event, maybe one of them ever in sports."