Trump Got Jokes! They're Terrible, Terrible Jokes That Say Much About How He Sees Himself and the World


On August 28th, Donald Trump took to Twitter to make what he clearly considered a hilarious joke, tweeting, “A sad day for the Democrats, Kristen Gillibrand has dropped out of the Presidential Primary. I’m glad they never found out that she was the one I was really afraid of!” 

By Trump standards, this was grade-A, first class, primo material. It wasn’t “funny”, of course, let alone hilarious or gut-busting but it was recognizably a joke with a clear-cut premise and a target delivered relatively cleanly for a man who generally has a devil of a time expressing himself in a lucid, comprehensible fashion. 

Like all of Trump’s “comedy” it’s all about punching down. Punching down is the essence of the joke. We’re supposed to titter deliciously at the absurdity of Donald Trump, a crazed narcissist egomaniacal even for an American president, a group of gentlemen who individually decided that they should be the most powerful person in the world, would feel threatened politically by Kristen Gillibrand, a candidate who began the race with a ten million dollar war chest but failed to develop any momentum and faded quickly before dropping out. 

The implication is that Trump is a Gulliver-like figure flicking away the silly lilliputians of the Democratic Party like the irrelevant nonentities they are, that he could not be more overjoyed about absolutely destroying whoever the Democrats run against him. Trump’s tweet pretending to be scared shitless of Gillibrand’s candidacy, but only her candidacy, may be mean and condescending and not funny but unlike most of Trump’s comedy, it at least reaches the level of being an actual joke. 


This places it far above most of Trump’s comedy, which can more accurately be described as saying cruel things in an ostensibly joking, light-hearted fashion. 

It’s less comedy than bullying in quasi-humorous form. Cruelty on an almost unfathomable scale is at the heart of Trump’s comedy. When Trump sneered “'I like people that weren't captured’, really zinging John McCain for the many years of torture he endured, he was making a joke. It was a heartless, sociopathic, utterly tone-deaf, bizarrely condescending joke but it was also intended to be hyperbolic and ridiculous to a comic extent. 

It was a joke and yet it was not a joke at the same time. That’s the hallmark of a Donald Trump “joke.” He’s joking and he means whatever horrible thing he’s saying simultaneously. Sometimes he’ll say something horrible and when it gets an appalled reaction he pretends that he was joking and being sarcastic, like when he referred to himself as “The Chosen One.” 

A good example of the schoolyard taunt level of Trump’s comedy can be found in the insulting names he gives his opponents both Democratic and Republican, real kindergarten-level stuff the public loved so much they catapulted him to the highest office in the land in angry defiance of God’s will. 

There’s the bland, boring, barely-trying mocking monikers, like “Sleepy Joe Biden” as well as insulting nicknames that none too subtly attack an opponent’s masculinity and virility, like “Little” Marco Rubio.

“Pocahontas”, Trump’s name for Elizabeth Warren, has garnered the most attention because it is transparently the most racist, sexist and just plain cruel nickname for an opponent Trump has come up with, and it’s his most overtly comic, in a crude, shock jock kind of way. That’s the level we’re at as a country: the president insults one of his biggest, most important and respected critics and political opponents using the kind of language that would get Billy Bob The Human Fart Machine of WPAR the Party Station That Rules The Nation called into the head office and chewed out because advertisers think it’s racist and insulting and are thinking of pulling spots. 


One of the most excruciating experiences of my professional life entailed reading The Art of the Deal for Silly Little Show-Biz Book Club. Tony Schwartz, the president’s ghostwriter and now fierce critic, had the unenviable task of replicating Trump’s repellent voice and disgusting personality. He accomplished that feat all too well, to the point that the book is pretty much unreadable. Part of parroting Trump’s voice involves injecting nothing in the way of humor that I can recall, beyond a reference to punching a teacher in the face as a boy and knocking him to the ground because he thought he didn’t know anything about music, but that was less a funny story than disturbing early evidence of Trump being a clear-cut sociopath 

Trump, is, after all, a man who regularly, non-ironically uses the phrase “lamestream media.” Lamestream media! And people think the dude is playing 5th-dimensional chess when he’s obviously not playing with a full deck, as his comedy stylings further prove. 

Or look at his last Saturday Night Live appearance. The “joke” of the sketches Trump chose all seemed to be that Trump was even cooler and more amazing than even he professed to be. It wasn’t self-deprecating or funny; it was self-aggrandizing, insufferable and unwatchable. Let’s just say there’s a reason I haven’t watched SNL since.


Whether Trump is being racist and unfunny, or just unfunny and cruel, one thing is for certain: Donald Trump’s bullying, nasty, nasty comedy is no laughing matter, in more ways than one. 

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