In it, but not of it. TPM DC
Trump's involvement with pro wrestling goes back more than a quarter of a century. In the beginning the logic was pretty simple: WWE was staging big events at Trump-owned venues, so he had a vested interest in promoting the "sport." But over time, Trump got drawn into WWE's staged storylines. And the logic there is pretty simple, too: As a showman, an impresario, an over-the-top, larger-than-life hero/villain, The Donald is in real life what pro wrestlers try to portray themselves as in the ring. It was a match made in promoter heaven.
Trump’s official relationship with WWE began in 1988 when he hosted WrestleMania IV at his Atlantic City Trump Plaza.
— CHEF CHRISTOPHER (@TheFoodFella) September 16, 2014
The event was so successful, Trump successfully lobbied for WrestleMania V to return to Atlantic City, the only time the top WWE event was held in the same place two years in a row. For WrestleMania V, Trump had 2,000 seats added to the venue, and with over 20,000 attendees broke the record for the largest event there, according to "30 Years of WrestleMania."
“We did so well in Atlantic City with WrestleMania IV that our customers demanded that we bring WWE back for WrestleMania V,” Trump said.
Trump continued to make appearances at various wrestling matches. In 2004, he was interviewed ringside by Jesse "The Body" Ventura, a former wrestler who had recently finished up his stint as Minnesota governor.
When Trump gave Ventura his endorsement for a possible White House run, one of the announcers joked that Ventura could use a billionaire as a vice president. But Trump’s and Ventura’s political relationship began much earlier. In the 2000 election, Trump sought the presidential nomination of the Reform Party, in part to aid Ventura in an intra-party war with Pat Buchanan, who eventually became the Reform Party nominee after Trump dropped out.
A fake “Donald Trump” had better luck when he wrestled “Rosie O’Donnell” in 2007. The real celebrities had been publicly fighting. The WWE match culminated with “Donald” (played by Ace Steel) smashing “Rosie” (Kiley McLean) with a fudge cake.
But Trump’s involvement in WrestleMania XXIII “Battle of the Billionaires” was a multi-episode, headline-making event. Trump’s and McMahon’s “rivalry” started in am episode a few weeks after the Rosie match, during “Fan Appreciation Night.” Via the arena Jumbotron, Trump interrupted McMahon’s emceeing to rain “thousands of dollars” (in his retelling) upon fans.
A few weeks later, Trump appeared on the show live to announce his bet with McMahon, and WWE teased the feud further in an episode devoted to a “contract signing” overseen by Stone Cold Steve Austin.
Outlets from the New York Post to CNN covered the lead-up to the showdown, and the pay-per-view showing, for which fans paid $44.95, broke company records by bringing in 1.2 million viewers.
In the end, Trump’s Bobby Lashley was victorious over the Umaga and McMahon was forced to have his head shaved by The Donald.
Their "feud" was played up again in 2009 when Trump “bought” Monday Night Raw from McMahon (a development Bloomberg and TVGuide treated as fact). Fans -- growing jaded by the WWE's over-staged antics -- were skeptical, and cable network USA, which aired WWE, copped that it was all an act.
"We intended the release to be promotional for that ongoing story arc on the series," USA said in a statement. "There is no such actual 'sale.' We apologize for any confusion."
Nevertheless, WWE teased out the narrative segments in which “The Apprentice” star “fired” the show’s characters and nonchalantly ordered around “The Boogeyman.”
Eventually McMahon “bought back” the Monday Night Raw, but not before Trump ran a ratings-busting episode of Raw commercial-free to show his appreciation for the fans.
Trump and McMahon’s lucrative relationship took a turn, however, during McMahon’s wife Linda's second try at a U.S. Senate seat in 2012, after her failed run in 2010. With Trump pushing the Obama “birther” conspiracy, Linda McMahon’s campaign attempted to distance itself from The Donald by denying that the WWE had donated $5 million to Trump’s charity in exchange for his WrestleMania appearances.
Whatever tensions that moment provoked between the McMahons and Trump were cooled by 2013, when Trump was inducted into the WWE Hall of Fame.