Donald Trump and WWE: How the Road to the White House Began at 'WrestleMania'

As he enters the Iowa Caucus cage match, we look back on The Donald's long history with Vince McMahon's wrestling empire

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Donald Trump; Vince McMahon; WWE Timeline
Donald Trump and Vince McMahon headline 'WrestleMania: Iowa.' Bebeto Matthews/AP

"Donald Trump is a 'WrestleMania' institution."

That's how Vince McMahon began his speech inducting The Donald into the WWE Hall of Fame in 2013, and while "institution" may have been pushing it (at least judging by the response Trump got when he took the stage), there is no doubt that both sides have had a long – and interesting – relationship, one that stretches back nearly 30 years.

It began long before Trump was a presidential candidate, or even the guy who fired people on reality TV, but as his bid to become the Heavyweight Champion of the Free World heads into the cage match that is the Iowa Caucus, we figured now was a good time to look back on the history that lead him to becoming a WWE Hall of Famer. And probably taught him a few tricks he's using on the campaign trail.

Trump and the WWE first crossed paths in 1988, a few years after the opening of the Trump Plaza in Atlantic City. In an attempt to turn AC into a true destination, Trump brought in WrestleMania IV ("Everybody in the country wanted this event, and we were able to get it," he boasted at the time). It went well enough that Trump made a successful push to bring WrestleMania V back to Atlantic City. It remains, to this point, the only time a city has hosted WrestleMania in back-to-back years. The Trump Plaza closed in 2014.

Trump would show up at several WrestleManias as a member of the audience, and was even interviewed in the crowd by Jesse "The Body" Ventura at WrestleMania XX in 2004. Ventura started things off by complimenting Donald's hair (it should be noted "The Body" was wearing a bandana atop his head), then the former Minnesota governor teased a return to politics by asking Trump if he'd support him on a run for the White House. This prompted Jerry Lawler to wonder if we could someday see a ticket that included Trump. And we all just laughed.

Of course, you can't talk about Trump's involvement in WWE without mentioning the Battle of the Billionaires. In 2007, Trump's feud with McMahon became a featured storyline at WrestleMania, but its seeds were actually planted months earlier (who says WWE can't do continuity?) In late 2006, Trump was engaged in a war of words with The View's Rosie O'Donnell, and in an attempt to capitalize, WWE soon hyped a match between the two on Raw. Two independent wrestlers (one of whom, Ace Steel, would sign a WWE developmental deal soon after) portrayed the celebrities in a segment that would quickly become one of the worst things WWE has ever aired. However, it was a sign of things to come.

Three weeks after the horrific Trump/Rosie segment, Raw held "Fan Appreciation Night," where McMahon would use the opportunity to deride ungrateful fans for their lack of respect, only to be triumphantly interrupted by Trump, who showed up on the TitanTron. Previewing his 2016 presidential bid, he said that McMahon wasn't giving the people what they wanted – and he had a plan to make WWE great again.

Using his powers of capitalism, Trump then proceeded to dump money – some of it actually real – on the audience, embarrassing McMahon in the process ("Donald Trump, you son of a bitch!" he bellowed). This segment would serve as the kick off to the feud known as the Battle of the Billionaires. A few weeks later, Trump would return to Raw, this time in-person, to challenge McMahon to a match at WrestleMania. Vince wouldn't accept, saying a doctor had advised him never to wrestle again due to previous injuries.

Instead, McMahon proposed that both men find others to fight for them – which wasn't enough for Trump, because, as he pointed out, "You're a rich guy, and I'm a richer guy." The only way he would accept the match was if the stakes were raised significantly, and, in the wrestling universe, that meant only one thing: A hair vs. hair match. Yes, Trump would put his iconic locks on the line if McMahon would as well, and Vince accepted after a little bit of goading.

The heelish McMahon picked the monstrous Umaga do to his dirty work, while Trump countered with ECW champion Bobby Lashley, and all was going swimmingly until a promotional appearance by Donald on Imus in the Morning, when he was asked about his supposedly hand-picked representative in the 'Mania match. He stumbled over his words, and then managed to answer "Bobby Lindsay… [a] Black gentleman, and the strongest man I've ever seen."

Unsurprisingly undeterred, Trump also showed up soon after on WWE TV to sign a contract for the WrestleMania 23 match. McMahon would be his usual boastful self, claiming that there was no way he could lose thanks to Umaga, and his own traits, including the size of his "grapefruits." Trump fired back with, "Your grapefruits are no match for my Trump Towers," which just raised so many questions.

While it was a pretty standard contract signing (Stone Cold cameo aside), there was one eerily prescient moment. After making their match official, Trump started touting his poll numbers, saying that "95 percent" of Hollywood celebrities – John Travolta was singled out – wanted to see him shave McMahon's head. He has employed the same strategy since announcing his candidacy for the White House this past summer.

WrestleMania 23 was a huge hit for WWE, shattering company records for ticket revenue and PPV buys, and while some of the credit has to go to a card that featured John Cena vs. Shawn Michaels and Batista vs. the Undertaker, Trump's involvement definitely gave the event a sizeable boost. On the night of the show, he shot a segment in which he no-sold the Boogeyman, then took on McMahon in a match that saw him tackle the WWE chairman and throw some of the worst punches in wrestling history. Oh, Lashley won, meaning Trump also got to give McMahon a haircut – before demonstrating he had no idea how to take a Stone Cold Stunner.

Trump would resurface on Raw in June of 2009, when a storyline had him swoop in and buy the show from McMahon. Trump promised some innovative ideas as he took over Raw, including running a commercial-free episode the following week. This actually helped ratings spike nearly a full point, though that was sort of offset by the fact that a fake press release announcing Trump's ownership actually caused the price of WWE stock to fall 7 percent. Of course, all of this was quickly rectified when McMahon bought back Raw for twice what Trump had paid for it (the Donald always wins), though given that this entire debacle also kicked off the hated "Guest Host" era of Raw, you could argue that it haunted wrestling fans for years to come.

And that brings us to that WWE Hall of Fame ceremony in 2013. While a few of his fellow "celebrity wing" members had been given the business by the crowd during their inductions – like Drew Carey in 2011no one got treated like Trump. The WWE faithful in New York booed Jerry Lawler, who was simply there to introduce Trump's inductor, McMahon. They booed McMahon whenever he mentioned Trump's name. And they booed Trump. A lot. Except when he introduced his daughter, Ivanka. Of course she got cheered.

Yet, it was at the Hall of Fame where Vince McMahon, in all seriousness, said the following: "When you think about it, second only to me, Donald might very well be a great president of the United States." The New York crowd booed. We'll see what the folks in Iowa have to say.

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