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The UFC Freedom 250 fight at the White House is hardly Trump’s first brawl

The last time notable combat sports were held at the White House, former President Theodore Roosevelt was hosting boxing matches, including taking up opponents himself. In one bout, he even took a blow to the face that left him partially blind in one eye.

Despite President Donald Trump’s past forays into the world of professional wrestling, he won’t be the one in the ring at the UFC fight scheduled to be held on the White House South Lawn.

But before taking office, Trump had long-running relationships with prominent figures in the world of combat sports. From boxing events at the Trump Taj Mahal in Atlantic City, New Jersey, to his friendship with boxing promoter Don King, Trump has long sought to make his mark on sport.

Donald trump, Mike Tyson, and Don king attend the March of Dimes Gourmet Gala on November 21, 1989 at the Plaza Hotel in New York City. Ron Galella / Ron Galella Collection via Getty Images

The match at the White House — part of a slate of events to celebrate the United States’ 250th birthday (although not to be confused with the congressionally sanctioned events known as America250) — is scheduled for June 14. The date, coincidentally, is Trump’s 80th birthday.

During a press event in the Oval Office with the fighters earlier this month, Trump (displaying a disregard for well-known trademarks) promised the event will be “the greatest show on Earth.”

“It’s never going to happen again,” Trump said. “Never happened before.”

Renderings from the UFC show a 5,000-seat arena, currently under construction on the South Lawn, that will sit underneath a red, white and blue arch. The White House and the UFC said invited guests and members of the military will sit around the octagonal cage, while screens will be set up at the Ellipse to show the fights to roughly 85,000 fans. Weigh-ins for the fighters are expected to take place at the Lincoln Memorial.

In a recent interview with The New Yorker, UFC CEO and longtime Trump ally Dana White said the president had floated the idea of fights at the White House while attending a recent fight. 

“He leans over to me in the middle of the fight and goes, ‘We should do a fight at the White House,’” White said. “I said, ‘Yes. Yes, we should. I’m in. I’m in!’”

Ties to White and UFC

Before White took over the UFC in 2001, mixed martial arts fighting was banned in a majority of states across the country. Speaking in support of Trump at the 2016 Republican National Convention, White said most arenas didn’t want anything to do with hosting UFC events. 

But, he said, Trump took a chance on the company and hosted the first and second matches of White’s promotion career at the Trump Taj Mahal. 

“Nobody took us seriously,” White said in a speech at the 2016 RNC. “Nobody, except Donald Trump.”

Over the course of their relationship, White has stumped for Trump at rallies, and he appeared again at the RNC during the president’s 2024 campaign, where White called Trump “the toughest, most resilient human being.” On election night in 2024, Trump invited White to speak on stage during the celebration.

Trump did a victory lap at a UFC fight at Madison Square Garden just 11 days after winning the 2024 election. In 2019, Trump made history as the first sitting president to attend a UFC match. Since his first term, Trump has sat cageside at seven UFC matches.

Two men fight in a cage match, while Donald Trump is seen through fencing
Trump, with UFC CEO and President Dana White (left) watch the Heavyweight match at Kaseya Center in Miami, on April 11, 2026. Jim Watson / AFP via Getty Images

Trump last attended a UFC fight in Miami on April 11, where he walked out grinning and waving to the stadium crowd.

And while Trump sat cageside with White, Vice President JD Vance announced from Islamabad that 21 hours of peace talks had failed to produce a deal to end the war with Iran.

Past with combat sports

From the 1980s onward, Trump frequently has hosted, sponsored and attended boxing and pro-wrestling events, cozying up to big names like boxing promoter King and his clients Mike Tyson and Muhammad Ali.

In 1984, Trump opened Trump Plaza, a casino and hotel, in Atlantic City. Soon after, he started sponsoring boxing matches at an adjacent convention hall where he hosted a number of Tyson fights. 

Trump later ventured into professional wrestling, hosting WWE events in the late 1980s and appearing at showcases through the early 2000s. He’s had a decades-long relationship with Vince McMahon, who co-founded WWE with his wife, Linda McMahon.

Two men in business attire fight in a wrestling ring
Vince McMahon and Trump square off at Wrestle-mania XXIII in Washington, D.C. on March 12, 2007. Sam Greenwood / WireImage for World Wrestling Entertainment, Inc via Getty Images

In 2007 and 2009, the WWE made contributions totaling $5 million to the Trump Foundation.

Linda McMahon has served in Trump’s Cabinet twice: as Small Business Administration administrator from 2017 to 2019, and as secretary of education in the current administration.

Throughout Trump’s multiple presidential campaigns, well-known combat sports figures have showed up in support. In addition to White and King, who attended the 2016 RNC, the late WWE wrestler Hulk Hogan stumped for Trump at multiple events during the 2024 campaign.

While speaking at the RNC that year after the assassination attempt in Butler, Pennsylvania, Hogan ripped off his tank top to reveal a Trump-Vance tank top beneath. 

“Let Trumpamania rule again!” Hogan exclaimed. “Let Trumpamania make America great again!”

The post The UFC Freedom 250 fight at the White House is hardly Trump’s first brawl appeared first on MS NOW.

Trump, Mike Tyson, and Don King attend the March of Dimes Gourmet Gala on November 21, 1989 at the Plaza Hotel in New York City.

Trump, with Hunter Campbell, Chief business officer of UFC, (2nd from the right) and UFC CEO and President Dana White (left) watch the Heavyweight match at Kaseya Center in Miami, on April 11, 2026.

Vince McMahon gets more than he bargained for when Trump got physical after signing the contract for Wrestlemania XXIII’s “Hair vs Hair” match at Monday Night RAW in Washington, D.C. on March 12, 2007.

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