In the late '80s, Donald Trump's Atlantic City boardwalk hotel hosted back-to-back WrestleMania events, and he and Vince McMahon became friends from there. Trump elaborated on his relationship with McMahon and the company, saying, "it all comes to fruition because of Vince, because he is a very unusual guy. Amazing guy."

Trump working with McMahon in the late-'80s wasn't just due to their friendship — he is a true admirer of the art of pro wrestling and a willing participant. Those who worked with him have had generally positive things to say about Trump, and Jim Ross, who spoke out in opposition to his politics, said, "Whatever 'it' is, Donald gets it, and he gets our business."

The Trump Plaza Hotel and Casino hosted WrestleMania IV (1988) and V (1989), setting a live gate and pay-per-view buy rate record that held for a full decade. Though both events were advertised as taking place at Trump Plaza, WrestleMania actually took place next door at the Historic Atlantic City Convention Hall and was sponsored and paid for by Trump.

Pro wrestling and reality tv have several similarities, and the way Trump used "The Apprentice" to bolster his fame runs parallel to how wrestlers use their platforms to become bigger stars and relate to the fans. When he finally entered the WWE ring, his transition from reality tv to wrestling was seamless.

At WrestleMania XX in 2004, Trump was interviewed by Jesse Ventura, drawing a mixed reaction from New York fans. He had little to say outside of remarking about his long-standing relationship with Vince McMahon, and when Ventura hinted at a return to politics, asking if he had Trump's moral and financial support, the future U.S. President replied, "100 percent."