Trump Locates the Limit of Assholery As a Political Strategy

The Asshole-palooza at Madison Square Garden didn't go over the way they planned.

If you’ve been wondering where the limits of assholery as an effective political strategy are, the Trump campaign may have just found it. Imagine if the “October Surprise” of 2024 turns out to be a hackish insult comic bombing on stage at a Trump rally, and turning just enough votes away from the Republican ticket to swing the election. 

That might or might not happen in the end. But the fact that the big story out of the most important Trump rally of this election was comedian Tony Hinchcliffe disparaging Puerto Rico shows that the Trump campaign is trapped in its malodorous little bubble. And after all the work they’ve put into getting funnier, there’s a lot about political humor conservatives still don’t understand.  

As you’ve no doubt heard by now, Hinchcliffe was one of Trump’s warmup acts at the big Madison Square Garden rally on Sunday. He ran through a list of digs at various ethnic groups — Black people eat watermelon, Jews love money, etc. — but the real attention-grabber was this line: “There’s literally a floating island of garbage in the middle of the ocean right now. Yeah. I think it’s called Puerto Rico.” 

Here’s his whole set, if you care to watch:

In short order, the world’s most famous Puerto Ricans — Bad Bunny, Jennifer Lopez, Marc Anthony, Ricky Martin — sent out endorsements of Kamala Harris to their quadrillions of social media followers, and the Harris campaign put out this ad:

Maybe everyone will forget about this in a few days, but early reports suggest otherwise: 

Republicans have attempted to distance themselves from the Puerto Rico joke, but notably, not from the rest of the racist and sexist things that were said at that rally (by Hinchcliffe and others), nor from the hateful things Trump himself says every day. Marc Caputo reports at The Bulwark that Hinchcliffe’s original script was even more shocking — yep, it included the C-word — and ironically, had that joke stayed in, it probably would have overshadowed the insult at Puerto Rico, which would have been much better for the Trump campaign. The news would have been “Comic Gets Vulgar At Trump Rally,” which would have been a much smaller story. 

The right still doesn’t quite get comedy

Hinchcliffe himself seemed a little lost — after some in the audience groaned at the Puerto Rico joke, he said “Normally I don’t follow the national anthem.” In other words, he hadn’t given thought to the audience or the context in which he’d be performing; he thought he’d give his regular schtick and people would laugh. In other words, he’s just not very good at his job. 

Perhaps the problem is that Hinchcliffe specializes in roasts, an old and very specific comedy genre. The point of a roast is that the person being roasted is there in the room, being mocked by people who know them; the question is how far the insults will go and whether the roastee can take it and keep laughing at themselves. Because the show requires the consent of the target, it’s all in fun. 

As I often do when the subject of political comedy comes up, I checked in with my friend Dannagal Young, an expert on the subject and author of Irony and Outrage: The Polarized Landscape of Rage, Fear, and Laughter in the United States. “Roast culture is completely outrageous,” she pointed out, where racism, sexism, antisemitism, and every other ism is not just tolerated but expected. “But everyone in that space goes in knowing that all the rules are suspended, and we go for the jugular.”

If you’re going to take the roaster out of the roast and put the same material in a different context, it just comes off like a bunch of lazy stereotypes, and it makes one suspect that the comic isn’t smart or creative enough to come up with anything else. What Hinchcliffe clearly doesn’t get is that it’s actually less offensive to toss a stereotype at one famous individual in the room with you — We all know my Jewish buddy here loves money, right? — than to say the same thing about a whole group that isn’t there. It just reads as mean, without any real humor behind it. 

In addition to being a roaster, Hinchcliffe is one of many comics today — mostly young white men — whose stock-in-trade is touching off the following exchange:

COMIC: Here’s something offensive!

EVERYONE: You’re an asshole.

COMIC: Oh, the woke libs can’t take a joke! I’m being canceled!

Comics like Hinchcliffe claim to be bold truth-tellers who are just too honest for the censorious left to handle. But what exactly is the profound truth that only they have the courage to share with their audiences? Puerto Rico is trash? Jews love money? Black people eat watermelon? They fancy themselves the heirs to Lenny Bruce, George Carlin, and Richard Pryor, but unlike those legends, they have nothing to say. They’re just hacks. 

And while conservatives are working much harder at comedy than they used to, and there are many more right-wing comedians out there — including some on television, like Fox host Greg Gutfeld — “They’re all just doing Rush Limbaugh, but they’re doing it on TV,” Young told me. “Nothing they do is ironic satire,” which is the kind of humor liberals find more appealing. “Most of what they do is exaggerated hyperbole. Every joke they do is Rush Limbaugh calling Sandra Fluke a slut.” Young hastens to add that “That doesn’t mean they’re not funny,” but it’s a humor built on punching down. 

And when you take that humor out of conservative-only spaces and put it on a stage where there are a hundred news cameras focused on you and everything you say will be clipped and delivered to the whole country, you may have a problem.

Is the asshole vote maxed out?

So why did the Trump campaign book Hinchcliffe in the first place? Two reasons. First, they are assholes themselves, and that’s the kind of humor they like. They’re rude and cruel and inconsiderate. They think empathy is a sign of weakness, human interactions are about dominance and submission, and if you aren’t the one dominating then you’re the weakling. When you hear, for instance, that Trump staffers’ response to being told by an employee at Arlington National Cemetery that they can’t shoot video in a particular area of the facility was to berate her, physically shove her aside, and then take to the media to slander her, your response is not “I would never have expected such behavior from Trump staffers,” it’s “Yeah, that’s how those assholes act.” 

And of course, there’s no bigger asshole than Trump himself, who sets the tone for everyone around him. But this predates him — for a long time, the most popular figures on the right have been assholes, from the biggest media stars (Rush Limbaugh, Bill O’Reilly, Tucker Carlson, Sean Hannity) to every aspiring douchebag who would like to join their ranks. Just yesterday one of those third-tier right-wing pundits was debating Mehdi Hasan on CNN and blurted out “I hope your beeper doesn’t go off” — Get it, you’re a Muslim, so it’s like you’re in Hezbollah! — which would have gone over great on Hinchcliffe’s podcast (but he won’t be returning to CNN).

Second, Trump and his aides believe that assholery is politically effective. They saw how millions of Americans thrilled to the permission Trump gave them to be their worst selves, not just racist and sexist but rude, loud, and belligerent. They know what happens in the parking lot at Trump rallies:

Craig Dumas didn’t hesitate when asked which one of his T-shirts sells best at Donald Trump’s rallies. It’s the one that calls the first female vice president a “hoe.”

“They love it,” said Dumas, 47, who in Tucson sold shirts insulting Harris with a misspelling of a derogatory term for a sexually promiscuous woman. “I can’t keep up with the count.”

Business was similarly brisk 2,400 miles away in Wilkes-Barre, Pennsylvania, where vendors hawked $25 versions of the shirts (“Say No to the Hoe”) down a line of attendees who smiled and snapped photos. Sold: to two parents who gave the shirt to their 13-year-old daughter. Sold: to a woman who wouldn’t wear it herself but knew her in-law would like it. Sold: to the Mikhailovs, who let their 14-year-old put it on and laughed as she talked about its meaning.

Imagine what kind of an asshole you’d have to be to buy a “Say No to the Hoe” t-shirt for your 13-year-old daughter.

For all that Republicans whine about how Democrats disrespect the GOP base, nobody has less respect for Republican voters than Donald Trump. Hillary Clinton may have said you could put half of his supporters into the basket of deplorables — “racist, sexist, homophobic, xenophobic, Islamophobic” — but Trump thinks all his supporters are in that basket. And he thinks there are even more assholes out there who might not vote, but if he cranks his own assholery up to 11, he’ll get them to the polls too. 

America has more than its share of assholes, but Harris is betting that they’re still a minority of the electorate. The reaction to the New York rally suggests she might be right. But Trump and his campaign are not going to make themselves any nicer. This is who they are.