Why have WWE legends Hulk Hogan and The Undertaker endorsed Donald Trump?

The Undertaker has become the latest WWE star to endorse Donald Trump.

Trump on Monday appeared on the hour-long podcast of Mark Calaway, known to his fans as The Undertaker.

This comes after WWE legend Hulk Hogan, real name Terry Bollea, showed up at the Republican National Convention earlier this year to endorse Trump.

But why are the WWE stars lining up to back Trump?

Let’s take a closer look:

Trump-WWE relationship

The relationship between Trump and the WWE goes back decades.

Trump’s hosted Wrestlemania IV and V – the WWE’s marquee event of the year at his hotel in Atlantic City – in 1987 and 1988.

Trump also made a guest appearance at Wrestlemania 7 in 1990 in Los Angeles.

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In 2007, nearly twenty years ago, Trump participated in the ‘Battle of the billionaires’ storyline with then WWE owner Vince McMahon.

McMahon, whose company merged with the UFC to form TKO, resigned from the company after sexual assault allegations against him emerged.

Trump picked wrestler Bobby Lashley to fight for him at Wrestlemania 27 against McMahon handpicked Umaga to be his representative.

The stipulation for the match was that either Trump or McMahon, depending on which wrestler lost, would have their head shaved as a result.

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Trump was seemingly nervous going into the event.

According to The Wall Street Journal, Trump in his contract made sure his head would not be shaved under any circumstances.

“Mr Trump had his associates review the contract to ensure that under no circumstances would Mr McMahon be allowed to shave his head, even if Mr Trump’s wrestler dropped dead in the ring,” the report stated.

The contract reportedly also mandated that McMahon give a charity chosen by Trump $4 million after the conclusion of Wrestlemania.

Wrestlemania 27, at that point, was the company’s biggest PPV ever.

“There were a lot of matches on that show,” wrestling journalist Brian Alavarez told BBC, “but people were super into the idea of one of these guys getting their heads shaved.”

“Fortunately, my guy won. And the loser had their hair shaved. I said, I don’t want to have my hair shaved!" Trump said on Calaway’s podcast.

Trump also offered Calaway praise.

“You had the best come out introduction I have ever seen in anything ever. It was so cool. The music, the lights, the best!” Trump said.

‘Master of this’

Calaway in turn gushed over Trump, saying he had made politics exciting again.

“You’ve been a master of this. You’ve got to make people care one way or another. Either they love you or they hate you,” Calaway said.

Calaway and fellow wrestler Glenn Jacobs – known as Kane – also put out a TikTok supporting Trump.

“All right everyone! November 5th, Electionmania. Choice is yours. You can go with President Trump, Kane and The Undertaker, or you can Kamala Harris, Dave Bautista and Tim Walz. Choose wisely. The nation depends on it,” Calaway said.

Calaway and Jacobs aren’t  the only WWE legend endorsing Trump.

So is Hulk Hogan.

Hogan earlier this year, speaking at the Republican National Convention in favour of Trump, urged America to “Let Trumpamania run wild, brother!”

Hogan told Fox News on Saturday, “Donald Trump is quick on his feet, man. He can pivot, he’s all smoke and mirrors, but when it comes down to business, he’s a businessman. You know, like that “economic forum”, where he schooled that guy who didn’t know a thing about tariffs?

“So I hear what you’re saying about the polls and it’s even-steven,” continued Hogan. “But let me tell you something, I don’t believe the polls. It’s going to be a landslide. You know, ‘too big to rig,’ brother, is the theme here.”

“I was one of these guys that was a coward. I was one of these guys that wouldn’t put a Trump sign on my yard, wouldn’t wear the Trump shirt, the Trump hat, because I was afraid what might happen or whatever. But after they took that shot and tried to kill him, that was it,” Hogan said earlier in September on Fox News.

“If you asked a man on the street if they know Hulk Hogan, even a non-fan is going to say yes. (Trump) is hitching his wagon to people that he thinks are big-time stars,” Alvarez told the BBC.

‘Total pro wrestling’

Some argue Trump’s foray into wrestling prepared him for politics.

Abraham Josephine Riesman, a freelance journalist and author of the book Ringmaster: Vince McMahon and the Unmaking of America, told BBC, “Those were the first times that Trump had ever given speeches to large, rowdy crowds that wanted red meat,” Riesman said.

Reisman, speaking to BBC about Trump’s strategy, added, “There’s a lot of people who listen to wrestling podcasts, and you’re going to get a lot of people who identify as apolitical or unorthodox.”

There’s a lot of people who stay away from politics and “just go with the most recent thing they remember,” Reisman added.

“He’s a character, a performer, and the things he says, the way he attacks his opponents, the way he puts himself over - it’s absolute total pro wrestling,” Alvarez added.

Interestingly, Trump also called the WWE to check if McMahon was okay after a storyline explosion killed off his character in 2007.

Trump and McMahon remains friends to this day.

According to reports, he takes calls with McMahon away from his handlers.

But not everyone WWE legend is pulling for Trump.

Dave Bautista, who is now an actor, slammed Trump in an advertisement on late-night TV host Jimmy Kimmel’s show slammed Trump as a “a weak, tubby toddler” who “wears more makeup than Dolly Parton”.

“A lot of men seem to think that Donald Trump is some kind of tough guy. He’s not,” Batista said.