Long before Donald Trump went head-to-head with Hillary Clinton on a debate stage or took a seat in the Oval Office for a second time, he was already making headlines in an entirely different kind of arena — the world of professional wrestling.
Back in 2007, at WrestleMania 23, Trump faced off against WWE owner Vince McMahon in what was billed as the “Battle of the Billionaires.”
And while the stakes may not have involved foreign policy or campaign promises, they were still, in their own outrageous way, sky-high — the loser was going to get his head shaved bald.
Wrestling Rings and Boardrooms Collide in a Billionaire Showdown
The spectacle kicked off as only WWE can do — with drama, theatrics, and a storyline that turned heads.
McMahon, known for playing the villain in the wrestling world, wasn’t thrilled about another wealthy outsider like Trump soaking up attention in his ring.
So, as the story goes, a parody skit between faux versions of Trump and Rosie O’Donnell sparked the idea to pit McMahon and Trump against each other in a hair-raising wager.
But the billionaires didn’t wrestle themselves.
Trump was represented by Bobby Lashley, the ECW champ at the time, and McMahon chose Umaga, an undefeated powerhouse.
The buildup lasted months, but the actual in-ring action only lasted 13 minutes.
Still, what happened during and after that match shook up wrestling — and possibly gave Trump a taste for high-stakes, high-drama entertainment that echoed through his later political career.
Trump Embraced the Chaos and Promised to Go All In
According to Lashley, Trump was all-in from the moment he arrived.
In an interview with Chris Van Vliet, Lashley recalled Trump saying, “This is your guys’ world.
I’m not trying to take over — just tell me how I can make it bigger.”
Whether it meant using Trump Tower or calling in favors, he was game.
That kind of showmanship blended right into wrestling’s DNA — and fit neatly with Trump’s flair for spectacle.
Unlike many celebrities who demand the spotlight, Trump was willing to play the part without overshadowing the performers.
The WWE team made sure to frame the story in a way that made everyone — even Trump — look like a star.
The Backstage Politics Were Just as Dramatic as the Match Itself
Behind the scenes, several different pairings were considered before Lashley and Umaga were chosen.
At one point, Shawn Michaels was in the mix to represent Trump against King Booker.
Another potential matchup involved Kane (Glenn Jacobs, now a Republican mayor in Tennessee) going against The Great Khali, possibly recreating the iconic Hulk Hogan vs. Andre the Giant moment from WrestleMania III.
The most lucrative idea? Trump being represented by Hulk Hogan in a clash against The Big Show — but that never came to be.
Instead, Lashley and Umaga carried the main event, and they did so with plenty of credibility.
Lashley is now a multi-time world champ and current AEW tag champion, while Umaga left a lasting legacy before his untimely passing in 2009.
Stone Cold Steve Austin Entered the Fray to Keep Things Wild
Adding another layer of star power to the match, Stone Cold Steve Austin was brought in as the special guest referee.
While neither Trump nor McMahon wrestled, they definitely got physical.
Trump even tackled McMahon and threw a few punches — a moment that would later reappear on social media during his presidency, with the CNN logo edited over McMahon’s head in a viral post.
Lashley shared that Trump’s big moment — the clothesline — wasn’t originally planned.
But somewhere along the way, someone gave him the green light, and the rest is history.
The Head-Shaving Was the Payoff, but the Beer Bash Was the Closer
Once Lashley pinned Umaga, it was time for the big payoff: Vince McMahon got his head shaved.
Trump, Lashley, and Austin lathered him up with shaving cream and took turns buzzing off his hair, while 70,000 fans inside Ford Field roared.
What followed was classic WWE — and classic Trump.
There was beer, celebration, and of course, a twist ending: Stone Cold stunned Trump with his signature move, leaving the future president sprawled out in the ring.
That clip is still proudly featured on WWE’s website.
Wrestling Gave Trump a Stage — and Maybe Some Political Strategy
Paul “Triple H” Levesque, now WWE’s Chief Content Officer, summed up Trump’s appeal during a recent interview.
He said Trump was charismatic, savvy, and knew how to get under people’s skin — a talent that worked well both in wrestling and politics.
“Why was he the billionaire who was on People Magazine every week?” Levesque asked.
“Because of his character, his showmanship, and the way he captivated people.”
Whether or not he learned that from wrestling, Trump clearly understood the power of being larger than life.
From Ringside to the White House — And Back Again
This wasn’t the only time Trump and McMahon crossed paths.
Linda McMahon, Vince’s wife, later became Trump’s Education Secretary.
The Trump Plaza hosted WrestleMania IV and V, and Trump even showed up at WrestleMania VII.
The two also teamed up on The Celebrity Apprentice, with Trump calling Vince “the greatest promoter he’s ever known.”
During one episode, McMahon was even eyeing combat sports legends Tito Ortiz and Lennox Lewis for potential wrestling cameos.
The boundary between business, entertainment, and politics was already beginning to blur.
A Lot Has Changed — But the Drama Never Really Stopped
Fast-forward to today: Vince McMahon has been ousted from WWE twice over sexual misconduct allegations (which he denies), and Trump is back in the White House for a second term, grappling with new political controversies — including a bizarre international prison mix-up involving an American man in El Salvador.
Still, the echoes of WrestleMania 23 linger. No one could’ve predicted how that outlandish “Battle of the Billionaires” storyline would ripple into the future of both men.
But if there’s one thing we’ve learned — whether it’s in politics or professional wrestling — it’s that spectacle always sells.