If pro wrestling is the folklore of the American working class, it's a strange folklore. The same form that gave us Dusty Rhodes's "Hard Times" soliloquy and the catharsis of watching a bald redneck live the dream by kicking the shit out of his boss also gave us regular doses of homophobia and racism. Think of pro wrestling as a family dinner, maybe, served at a huge table at which your cool, fun family members are seated with the conspiracy theorists and bigots. You're sitting there in the middle, head spinning, as you go from conversations about football and whether turkey sucks to whether the Bilderbergers are behind Syrian immigration to the United States.
That is, it's a milieu in which Donald Trump makes total sense.
It's no accident that Trump honed his current persona during his sporadic appearances with WWE. The Donald lashing his style to a pro wrestler's largeness has been pointed out recently by more than one person. At the same time, it's worth bearing in mind just how full of shit Trump is. Vince McMahon may be out of touch with his audience these days, but he has at least some lived experience as something other than insanely rich guy—experience that gave him a certain firsthand insight into his audience's id. Trump is faking it, always. This is a guy born into wealth who likes to pretend as hard as he can that he made it on his own through sheer will to power and a pair of extremely luxurious 4XL testicles.
In other words, Trump is pure heel, which makes it all the more perverse that his appearances on WWE, in the course of a multi-year—and, truth be told, pretty boring—feud with McMahon, always placed him in the role of babyface. It's a mark of the decline of WWE's product over the years that the dynamic that once pitted workers like "Stone Cold" Steve Austin against their bosses now slips into story lines about who is the richest guy with the biggest dick in the last monopoly in entertainment. Watching Trump versus McMahon during the feud's intermittent flare-ups is like watching two Martians argue about cricket: you might catch a bit of it, the words mostly make sense, but it is so hugely abstracted that you can't help but wander off and do something else.
Wrestlemania XXIII revolved heavily around their feud. It was, as WWE put it, "the Battle of the Billionaires," with Trump picking Bobby Lashley, now a TNA wrestler, as his proxy and McMahon choosing the Umaga, who is sadly deceased.
Trump and McMahon were angry at each other for mysterious reasons involving fading testosterone, but not angry enough to actually go at each other personally. It doubled as a hair vs. hair match, with the loser having his head shaved. Umaga lost and McMahon gamely had his head shaved, in part because shaving Trump's ridiculous honey-bun haircut is the equivalent of clearcutting Yellowstone—an offense against one of our great natural resources.
Looking back, the feud kicked off with a moment that anticipates Trump's current Mussolini With Hairplugs gimmick: Trump shows up on the big screen and makes money drop from the sky. Real money, 20s and 50s and 100s, drifting down from the rafters into the crowd. All the while, Trump barks semi-coherently at McMahon about how much he appreciates the crowd.
Why? We don't know. It's Trump's magic act, then and now: he snaps his fingers and disappears your problems through the force of his personality, which is effectively that of a $50 bill that has learned how to read WorldNetDaily.
Trump never got owned in a wrestling ring, sad to say. The closest we got was Steve Austin giving him a Stone Cold Stunner after the Lashley-Umaga match. Trump stands in the ring, awkwardly sipping a beer, before Austin delivers his finisher. Trump can't sell it worth a damn—he's magic, but not that magic—but he took it. Austin recalls that Trump didn't have to take the Stunner, but volunteered. He wanted to. It remains the most admirable thing Trump has done as a public figure.
As cool as it is for a rich guy to debase himself for our amusement—and it is extremely cool—there's a dark mirror in Trump of the guy who never outgrows the capacity to relate to others. In Trump, there's a deep, dark sociopathy to his act; he lives on that knife's edge between the entertainer and the madman, with some serious kayfabe-versus-reality issues. Trump takes the act on the road and seemingly doesn't care that the physical drama of the ring keeps turning into beatings of minorities by his proto-fascist entourage. Anyway, the political world already has its Battle of the Billionaires, every day. Sadly, there's no way to switch the channel on that one.