As the Octagon sits ready on the South Lawn of the White House, 25 years of blood, loyalty and mutual ambition are about to find their grandest stage on Sunday night.
UFC Freedom 250 – seven fights, two world title bouts and a crowd just yards from the Oval Office – is the most visible symbol yet of one of sport’s most unlikely partnerships.
But to understand how combat sports ends up on the president’s lawn on his 80th birthday, you have to go back to a different Trump property, a different era in UFC chief Dana White’s life, when neither man was quite what they are today.
It was November 2000 when everything quietly began. The Trump Taj Mahal in Atlantic City. Five thousand fans. A sport that 36 states had banned, dismissed by senators as ‘human cockfighting’ and shunned by every major arena in the country.
UFC 28 was the promotion’s first sanctioned event, held at the Taj Mahal – a hotel and casino owned by Donald Trump. Dana White attended that night not as a UFC official, but as the manager of fighter John Lewis.
He was accompanied by Lorenzo Fertitta and Frank Fertitta III, brothers who were Las Vegas casino owners and trained in jiu-jitsu under Lewis. In the crowd that evening, the three men looked at what was in front of them and saw a promising future.
Dana White and Donald Trump have built an unlikely friendship over nearly three decades
The UFC will host ‘UFC Freedom 250’ on the White House’s South Lawn on Sunday evening
Two months later, Zuffa LLC purchased the UFC for $2 million and named White its president. Almost immediately, he needed somewhere to fight and, after struggling to secure venues, Zuffa reached an agreement with Trump to use the Taj Mahal.
Trump himself has never been modest about what that meant. ‘They couldn’t get a venue because of the danger, you know,’ he once said. ‘People thought it was dangerous… and I gave them venues early on.’
Lavie Margolin, author of Ultimate Fighters: Donald Trump, Dana White and UFC’s Road to the White House, has spent years unpicking exactly what happened in those early days – and the myths that have grown around them.
The story White has told, of Trump personally calling to rescue the UFC and striking a deal that saved the promotion, doesn’t quite hold up to scrutiny. The venue was already booked when White took over and the footage from those Atlantic City shows? Trump’s nowhere to be seen.
‘Dana White has said many times that Donald Trump came for the first fight and stayed till the last fight,’ Margolin revealed. ‘But if you watch UFC 28, 30, 31 – you can’t find a picture with him. You don’t see him on screen at all.
‘What I think Dana meant to say was that for UFC 32 at the Continental Airlines Arena, he attended, stayed for every fight and things were off and running from there.’
For the first time, at that June 2001 event at the 20,000-seat Continental Airlines Arena, the broadcast showed Trump cageside. The myth had found its truth.
A real estate mogul who’d made his name hosting WrestleManias and Mike Tyson fights was lending his presence to a sport that still desperately needed it.
Trump played a pivotal role in the UFC’s development during the organization’s early years
‘People thought it was dangerous… and I gave them venues early on,’ Trump once explained
Trump, pictured at a UFC in April, was first pictured cageside at UFC 32 back in June 2001
White later told ESPN: ‘He is one of my very good friends’ – one of just ten people in his innermost circle. But the roots of that friendship, Margolin suggests, run deeper than business.
‘Dana White’s mother wrote a book on Amazon,’ Margolin told me. ‘The whole book is basically saying what a terrible person her son is. He comes from trouble.
‘Donald Trump is 23 years older than him. He’s a very strong authority figure. You could clearly draw the parallel. It’s kind of more than a friend, it’s kind of a father figure.’
For years after those Atlantic City shows, the relationship went quiet. But it never went cold. Around 2012 and 2013, as Ronda Rousey was breaking through as a mainstream star, Trump would cut her UFC profiles out of the New York Times.
‘Like an older person tends to do,’ Margolin added, Trump would mail them to White with handwritten congratulations, in a means to keep the friendship going.
Then came the politics. When Trump ran for president in 2016, White was one of the loudest voices in his corner, speaking at the Republican National Convention. That moment, Margolin argues, transformed what had been a sporting relationship into something far larger.
Key to that transformation was a UFC staffer named Stephen Cheung. ‘He came on board around Trump’s first candidacy,’ Margolin explained. ‘He understands how to harness people, how to portray Trump in the right light rather than through mainstream media.’
It was Cheung, Margolin believes, who helped engineer Trump’s appearances at UFC events, his fluency with fighter names and storylines, and ultimately his route to podcasters, the manosphere, and Joe Rogan – whose endorsement of Trump became one of the defining cultural moments of the 2024 election cycle.
When Trump ran for president in 2016, White was one of the loudest voices in his corner
Trump and White pictured back in 2020 ahead of a ‘Keep America Great’ rally in Colorado
Trump has become a regular fixture cageside, pictured here with Kid Rock and Elon Musk
‘When he endorsed him,’ Margolin said of Rogan, ‘that was a really strong thing. And later you’d see the liberal media being very negative on it: “You’re not going to get disaffected young men to go out and vote.” And then they were like, “Who are our influencers going to be? We’re going to have to learn from this.”‘
The UFC’s fanbase – diverse and often oversimplified – had become a genuine political asset. And after January 6, 2021, when corporations and celebrities distanced themselves from Trump en masse, White stood firm.
He didn’t scrub Trump from the promotional material and keep his head down. He walked Trump into arenas. He made him visible at a moment when visibility was a statement.
The fighters on Sunday’s card carry that same loyalty. Justin Gaethje, who faces Ilia Topuria in the main event for the lightweight title, is defiant about where he stands.
‘I can’t explain to people how big of a fan he is of this sport,’ Gaethje told us. ‘He only wants to talk about fighting – and he’s normal! When it comes to fighting, he was pivotal in our start. Nobody would let us fight and he went against the mainstream. I love winners and he’s a f***ing winner.’
Bo Nickal, who fights on the undercard, has a relationship with Trump that goes back further than most on the card. ‘First time meeting Trump was in 2019,’ he said.
‘I won an NCAA championship and we all got invited to the White House. He really gravitated towards the wrestlers, which was so cool. I got to talk with him for a bit and I told him I was going to fight – he actually asked to be my manager.’
The story doesn’t end there. Fast forward to one of Nickal’s early UFC fights. ‘He was in the crowd, I saw him, gave him a nod, won the fight – and then he said, ‘Let’s go golf!’ I’m not much of a golfer so I didn’t know what to expect.
Four of the UFC stars set to fight on the South Lawn visited the Oval Office back in May
Lightweight star Ilia Topuria stands alongside Trump ahead of the inaugural UFC Freedom 250
‘But it was unbelievable. The coolest part is that we were able to just talk and chat very normally. He’s very humble and very real – I appreciate that.’
Derrick Lewis, the heavyweight fan favorite who also features on Sunday’s card, was more blunt about his allegiance. Asked what it’s like to be Trump’s favorite fighter, he barely let the question finish. ‘You mean his favorite pet?’ he said with a laugh.
‘Even before he became president the first time, I was a supporter of him. You know, before everybody got so crazy with the politics. There’s old videos out there with me supporting Trump, writing “vote for Trump.” I just like the guy. His character.’
The event itself has not been without controversy. A federal lawsuit, filed just days before Sunday’s card, called it a ‘volcano of corruption’ – the first private, for-profit sporting event ever held on White House grounds.
A federal judge rejected the motion to block it, noting that the UFC had invested $60 million in the event and that the plaintiffs had waited until two weeks after visible construction began to seek emergency relief.
Whatever its flaws, the sheer fact of UFC Freedom 250 is extraordinary. A sport that was once described in the US Senate as a form of legalized brutality, that couldn’t rent a ballroom in 36 states, that needed the hospitality of a failing Atlantic City casino just to survive – that sport is now fighting on the most famous lawn in the world.
On the president’s birthday. As part of America’s 250th anniversary celebrations.
The UFC hosted their UFC Freedom 250 press conference at the Lincoln Memorial on Friday
Thousands of fans will flock in from across the country to watch the once-in-a-lifetime event
The event will take place on Trump’s 80th birthday and in his own backyard
‘On its face, it’s kind of amazing,’ Margolin reflected. ‘If you look back at the early UFCs and even the darker days once they got kicked off TV, it was so low-rent.
‘Just the terms the media would use to describe them – “low IQ parents,” the lowest of the low. And the fact that we’re here is incredible.’
From the Taj Mahal to the South Lawn. From nobody would let them fight to nobody can stop them. Twenty-five years of Trump, White, and the UFC – and it started with a casino owner who saw something worth backing when everyone else looked away.
Sunday night, he gets to watch it from his own backyard.
