From hosting two WrestleManias, taking a “Stone Cold Stunner” in front of tens of thousands of fans and now bringing Linda McMahon into his Cabinet, Donald Trump’s relationship with professional wrestling dates back 30 years — and analysts say the president-elect’s close ties to WWE helped him hone his boisterous, over-the-top political persona.

Mr. Trump throughout his business career has been remarkably comfortable in and around a World Wrestling Entertainment ring, and the bonds he has forged with Vince McMahon — a fellow billionaire who turned what had been the regional WWWF promotion into a massive global brand — now have extended to politics.

Ms. McMahon gave millions of dollars to PACs supporting Mr. Trump’s campaign, and the family donated money to his foundation.

Mr. Trump responded by tapping Ms. McMahon, a Republican who mounted two unsuccessful U.S. Senate bids in WWE’s home state of Connecticut, to lead the Small Business Administration.

Although there has been no formal connection between Mr. Trump and the McMahons in nearly a decade, analysts say the incoming commander in chief owes the wrestling tycoons a debt of gratitude for, if nothing else, giving him a platform to promote his brand and offering him hands-on lessons in how to captivate an audience.

“You could argue that he was very performative in many of the same ways a pro wrestling personality was,” said Sam Ford, a research affiliate at the Massachusetts Institute of Technology’s comparative media studies program.

Mr. Ford, who follows WWE extensively, noted similarities in Mr. Trump’s political rise and the McMahons’ construction of a worldwide wrestling empire.

“They’re both involved in sort of modern-day myth-making of themselves,” he said. “You think of how Trump refers to himself and his empire, and the fact that WrestleMania was referring to itself as the meeting place of the gods, the immortals you can see that type of impresario, P.T. Barnum-like, carnival barker mentality in how both of these worlds were created.”

Mr. Trump and WWE first crossed paths three decades ago when both were beginning to cement their brands.

In March 1988, Mr. Trump hosted WrestleMania IV at Trump Plaza in Atlantic City, New Jersey. The landmark event — which included a rematch between Hulk Hogan and Andre the Giant — continued the wrestling promotion’s rise into mainstream pop culture.

It also coincided with Mr. Trump’s national profile. Five months earlier, he released his best-known and most successful book, “The Art of the Deal.”

The event was such a commercial success for both sides that Mr. Trump hosted the next year’s event, WrestleMania V, again at his Atlantic City casino.

Those events were key to furthering the rapid growth of what was then called the WWF. The promotion changed its name to the WWE and acknowledged that professional wrestling was a staged entertainment show, not an athletic contest.

Ms. McMahon’s role in propelling the company has prepared her for a role in government, the president-elect said.

“She helped grow WWE from a modest 13-person operation to a publicly traded global enterprise with more than 800 employees in offices worldwide,” Mr. Trump said this month when he nominated Ms. McMahon. “Linda is going to be a phenomenal leader and champion for small businesses and unleash America’s entrepreneurial spirit all across the country.”

Nearly 20 years after WrestleMania IV, when Mr. Trump’s stardom hit new heights with the hit TV show “The Apprentice,” he again did business with the McMahons. In the run-up to 2007’s WrestleMania 23, Mr. Trump frequently appeared on WWE television to hype the “Battle of the Billionaires” with Mr. McMahon.

The two businessmen didn’t face off in the ring. Instead, they selected wrestlers to compete on their behalf. The one whose hand-picked combatant lost would have his head shaved.

Leading up to the event, the interplay between Mr. Trump and Mr. McMahon on the company’s flagship TV show, “Monday Night Raw,” was as crass and outrageous as one might expect from two outsized personalities.

“He knows I have the grapefruits to give him a patented Mr. McMahon billionaire bitch slap,” Mr. McMahon said during one exchange.

“Your grapefruits are no match for my Trump towers,” the future president-elect responded, drawing wild cheers from the crowd.

At WrestleMania, Mr. Trump’s protege was victorious and, with an assist from special guest referee “Stone Cold” Steve Austin, he shaved Mr. McMahon’s head bald.

But Mr. Trump did not escape unscathed — he ended up taking a “Stone Cold Stunner,” Mr. Austin’s signature finishing move.

The event was a massive commercial success and remains the second most watched WWE pay-per-view in history, largely because of the media attention generated by Mr. Trump’s involvement.

“Trump was there to generate mainstream interest in WrestleMania,” Mr. Ford said.

Moving forward, WWE officials have openly discussed how remarkable it might be to have a U.S. president re-enter the ring.

“Wouldn’t that be something, see who gets their head shaved?” Paul Levesque, known to wrestling fans as Triple H, told CNBC this month when asked about a possible Trump return to WWE.

Now a top official with the company and husband of Mr. McMahon’s daughter Stephanie, Mr. Levesque described the incoming president as a “great friend” to WWE.

“We’ve done a lot with Donald Trump over the years. He’s been a great supporter of WWE, he’s been a great friend to us. We’ve had events at his building. He’s been a participant at WrestleMania,” he said. “It’s great to see him have the success he is having.”

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