Trump can't take a joke. So, eventually he did run for president, and after actually winning, he wouldn't attend because even though you get to stand at the podium and give it back, you have to have comedians and other attendees roast you first. You also have to acknowledge journalists as human beings, and Trump might slip up and use the German phrase for "lying press," if you know what I mean... Trump actually sat through a Comedy Central Roast years ago, and imposed a rule as a condition for his participation. No jokes about how he wasn't as rich as he claimed. They could joke about other stuff, but not that. That was off-limits.
Gee... I wonder what would happen if he wound up president with a sufficiently brazen comedian. First, would he attend the Correspondents' Dinner? Of course not. His skin defies current models of physics because no material larger than an atom should be thinner than an atom. Atoms are not supposed to be compressible, so... what's the deal with how thin his skin is?
Anyway, of course he'll skip. This year, the comedian leading the ceremony was Michelle Wolf, and she was even more caustic than the legendary routine by Stephen Colbert.
She drew blood. Note two things. First, she went there with Trump. She brought the audience into a "how broke is he?" routine. Nothing pisses Trump off more than challenging his assertions of wealth. Call him racist. Call him misogynist. Call him stupid. Incompetent. Ugly. Impotent. A rapist.
The one thing that is guaranteed to piss him off more than anything else is to challenge his assertions of wealth, and not only did Wolf do it, she got the audience to help her. Damn.
How funny were those jokes? They varied, but the real humor is in the fact that she made those jokes, and the observation that those really are the ones that piss off Trump the most.
Yes, her audience was Donald Trump, and her goal was to hurt him as much as possible, so she wrote jokes and structured them in a way that maximized the psychological damage they would do to him. Attack his wealth, and bring the audience in on it. Don't just make the audience laugh at his assertions of wealth-- have them participate. This really is his nightmare.
Remember, when he did the Comedy Central Roast, it was his contractual rule-- no jokes about his wealth.
Next, Wolf made a real observation at the end about the toxic-symbiotic relationship between the press and Trump. Donald Trump is entirely a media creation. He isn't a businessman. He just plays one on tv. He has been cultivating a celebrity image for decades, and the press failed in 2016 because of the image they created. They had no idea how to cover someone whom they had built up, whom they had made famous for no real reason, who lied about everything, and crossed every line imaginable. But, they made money off of him. She's not wrong on that. And every time Donald Trump says something stupid and vile, they still have a dilemma. How much do they focus on that rather than, oh, say, policy? What the fuck is happening with North Korea? Is this for real? I don't know, and I'm writing about a comedian making fun of Trump's bank account balances. Then again, I specialize in American politics rather than international relations, so I'll throw some game theory at that soon, but this is more in my wheelhouse. Still, Wolf makes a real point. Trump wouldn't be where he is without the press building him up and covering the stupid shit he says in irresponsible ways rather than things of real importance...
... I write as I spend my Sunday morning discussing a comedy routine...
