Looking Back At Donald Trump’s WWE Career

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Donald Trump and Vince McMahon

The WWE Hall of Famer and billionaire businessman has been in and out of the company’s storylines for years. Now, if somebody could only break it to him that being president of the United States is not a reoccurring WWE storyline.
(Photo : Bill Pugliano | Getty Images News)

Donald Trump has turned this 2016 presidential race into an ongoing saga right out of World Wrestling Entertainment.

Whether it’s him being downright crass, insulting his competition in the GOP or his willingness for a give-and-take with attendees of his rallies and media, alike, it’s almost as if Trump is auditioning to be a WWE Superstar … except he’s attempting to run for president of the United States.

Trump injecting WWE-like tactics in the race to become commander-in-chief isn’t a far-fetched claim, either, especially considering the business magnate has a rich history with the sports entertainment giant — one that dates back to March 1988, when he hosted WrestleMania IV in Atlantic City, N.J., before doubling-down and hosting WrestleMania V in AC as well.

And that’s just the beginning of Trump’s noted history with WWE. Here, we look back at some of his more notorious moments with WWE. After all, Trump is a WWE Hall of Famer and who could forget the sight of him shaving company owner Vince McMahon’s head in the middle of the ring at WrestleMania 23 in Detroit nearly 10 years ago?

By the way … Trump was in Detroit again last night, spouting more noise during a Republican debate. We can’t believe this guy is really running for president. If elected, he’s literally going to bring WWE to the White House!

Trump Hosts WrestleMania IV And V

Having successfully hosted prize fights in boxing at the Trump Plaza in Atlantic City, N.J., Trump was still looking to establish his newest property and Atlantic City overall as a hotbed destination for big-time events. That’s precisely why Trump made sure that his Trump Plaza was the official sponsor of the then-World Wrestling Federation’s “Show of Shows” for WrestleMania IV and WrestleMania V at the Atlantic City Convention Hall in 1988 and 1989.

The sports entertainment company was coming off the huge success of WrestleMania III and needed to hit hard and keep its momentum going in the subsequent years.

You can easily spot Trump front and center ringside during WrestleMania IV at the Atlantic City Convention Hall, where he watched Macho Man Randy Savage successfully defeat four opponents to win the World Heavyweight championship. Take a look.

A year later and it was as if Trump never left the Convention Hall, glued to the same seat, this time to witness the Mega Powers explode, with Hogan defeating Savage for the World Heavyweight title at WrestleMania V. With Trump Plaza sponsoring, The Donald was able to pull off Atlantic City being the only city to ever host WrestleMania in back-to-back years. Again, it’s pretty easy to spot Trump in any clip. See for yourself.

Trump Awestruck By Chuck Norris And The Fonz

Now a veteran of WrestleManias, Trump made sure to get a little face time during a live interview spot at the Los Angeles Memorial Sports Arena in March 1991 for WrestleMania VII. Just look at Trump’s face light up when meeting Chuck Norris, while “Mean” Gene Okerlund conducts the interview. Just to Norris’s left is Henry Winkler. Trump, Norris and The Fonz. What a trio. We’d take Norris as president over The Donald, any day.

Jesse Ventura “The Body” Interviews Trump At WrestleMania XX

On one hand, there’s Jesse “The Body” Ventura, former WWE Superstar, who shockingly served as the 38th governor of Minnesota from 1999 to 2003. On the other hand, there’s Donald Trump, longtime businessman and TV personality, who shockingly uses WWE-type microphone banter to run for president of the United States.

Well, way before Trump made his political aspirations known — you know, when he was busy hosting The Apprentice — he was the interview subject of Ventura before a packed Madison Square Garden crowd in New York City for WrestleMania XX. Trump praised friend Vince McMahon in the short interview, but we thought it was especially funny that Ventura complimented the businessman’s hair, while putting him on the spot to see if he’d fund his own presidential bid. Unbelievable.

Donald Gives Vince’s Money To Fans

How do you upstage a fellow billionaire? By giving away his money on his show. That’s exactly what Donald Trump did during a late-January 2007 episode of Monday Night Raw, where he upstaged Vince McMahon, making thousands of the WWE owner and CEO’s dollars rain on fans. The wild frenzy of a scene came on “Fan Appreciation Night.”

The moment would pave the way to the infamous Battle of The Billionaires between Trump and McMahon at WrestleMania 23 less than three months later. What’s funny — not to mention, phony — about this clip is when Trump looks back to showering fans with Vince’s money, it’s almost as if he’s reading from a teleprompter. Check it out.

Battle Of The Billionaires’ Contract Signing

Leave it to a couple of billionaires to turn a wrestling ring into a boardroom. That’s exactly what Donald Trump and Vincent Kennedy McMahon successfully pulled off during an episode of Monday Night Raw on The Road to WrestleMania back in 2007, when they officially signed the contract for “The Battle of The Billionaires.”

The rules were simple — Bobby Lashley would represent Trump and Umaga would rep McMahon in their match, with the winning billionaire shaving the loser’s head. None other than Stone Cold Steve Austin would be the ref. The contract signing ended with Trump rather weakly pushing McMahon, with the WWE owner dramatically over-selling the shove. If Trump can’t push hard in a WWE storyline, how is he going to push back upon terrorists?

Billionaire’s Bizarre Encounter With The Boogeyman

Waiting in the wings of the locker room, alongside former Miss USA Tara Conner, Donald Trump immediately started complaining about Vince McMahon not feeding him. With Trump growing impatient backstage during WrestleMania 23, his locker room abruptly turned into a red-light not-so-special scene, with The Boogeyman surprising the billionaire with an impromptu “Old MacDonald Had a Farm” nursery rhyme.

Freaked out, Conner quickly ran away, but Trump stayed put, almost causing us to wonder who’s more red in the face — Donald or The Boogeyman? Trump bombastically orders The Boogeyman to get him food, which got us thinking … if Donald can’t successfully order The Boogeyman to get his food, how in the world is he going to cut deals with the world’s tyrants?

Trump Wins Battle Of The Billionaires

A bet’s a bet … and unfortunately for Vince McMahon, he came up on the losing end at WrestleMania 23 and subsequently had to lose his hair. The ever-smug Donald Trump first used a buzzer, before dousing McMahon’s head with an insane amount of shaving cream and going to town with a razor, while McMahon was held down by Bobby Lashley and Stone Cold Steve Austin. The bald billionaire — Vincent Kennedy McMahon.

Stone Cold Stuns Trump

Hey, Stone Cold Steve Austin could always say he stunned not one, but two billionaires. Although Donald Trump won the Battle … he may have lost the war, with Austin dropping the mogul with a Stunner after banging beer cans in a toast. Don’t Trust Anybody, Donald!

The Donald Gets Raw

No matter how hard Donald Trump tries to stay away, the WWE keeps calling him back. That was the case in 2009, when Vince McMahon came up with this harebrained storyline to announce that he has sold the company’s flagship show, Monday Night Raw, to Trump. What a painful three-hour Raw to stomach for the WWE Universe.

Trump Fires Santino Marella

Hey, Santino … we mean, Santina … YOU’RE FIRED! Just like that, Donald Trump laid down the law as one of his first lines of duty as the new owner of Monday Night Raw. But Donald, running the country won’t be as easy as firing Santino Marella. We promise you.

Trump Sells Raw Back To McMahon

Shortly after The Donald purchased WWE’s flagship television show, he shrewdly drove up the value, demanding that Vince McMahon pay him double the price to get Monday Night Raw back. Once the handshake deal was completed in 2009, the WWE Universe let out a collective sigh of relief that they would never be put through the torture of seeing Trump on Raw so often.

Trump Honored In WWE Hall Of Fame

With all of Donald Trump’s history with the WWE, the company felt compelled to cement his legacy by enshrining him into its Hall of Fame back in 2013. But now that WWE has seen the nonsense that Trump has been spewing during the presidential race, wouldn’t it be a better move to scrub his name clean from the Hall of Fame? Vince McMahon should call his friend and tell him, “Donald … YOU’RE FIRED! You’ve got no chance in hell in being named back to the Hall again.” 

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