On this much, I agree with the likely sentiments of Tony Hinchcliffe, the comedian, podcast host and newly designated Republican martyr: It’s hard to get a solid laugh by calling Puerto Rico a “floating pile of garbage.”

He tried that one at Donald Trump’s rally at Madison Square Garden in New York last Sunday. He tried this one, too: Noting a Black attendee in the audience, Hinchcliffe resurrected a galling racist trope for a line about him and his Black friend “carving watermelons together” for Halloween.

That one got a free pass, for whatever reason. The floating pile of garbage joke did not. In the time it took Hinchcliffe to shill for Trump champ Mike Lindell’s MyPillow (“I bought four of ‘em!”) in the six-hour rally’s opening act, panicky texts between elected Republicans nationwide and members of the Trump reelection crew flew like the wind. Apologize! Marginalize! Distance Trump from that comedian, stat!

By late Sunday Hinchcliffe had been hung out to dry.

“Poor taste” is how Trump campaign spokesperson Karoline Leavitt described the Puerto Rico slag to Fox News. “Obviously that joke does not reflect the views of President Trump or the campaign.” Obviously.

Adding comic insult to an insult comic’s injury: Late Monday, NBC News posted a story about Hinchcliffe trying out some of his rally material Saturday night at a Manhattan comedy club. The comic’s jokes about rock-throwing Palestinians and money-grubbing Jews and garbage islands in the Caribbean drew “a handful of awkward chuckles,” according to an NBC employee in attendance that night. Hinchcliffe told the comedy club audience he wasn’t concerned, and that the racial stuff would work fine “tomorrow at the rally.”

For so many working comedians right now, whatever their politics, the last few years have been ripe for private and sometimes public mourning. Mourning for the days when jokes were jokes, and men were men and comics were, too, mostly. And nobody ever felt offended. And other lies.

Watching Trump’s rally jester Sunday, it struck me that Hinchcliffe’s problems begin and end with an apparent, chronic aversion to the two words behind some of the greatest comedy to come out of Chicago improv over the last 70 years.

The words are: punch up. Not down, like a bully. Up, like David vs. Goliath. Up, somewhere north of Hinchcliffe at the Garden on Sunday, at one low point mocking the imaginary sight of desperate migrants fleeing their homelands for an attempted border crossing.

This is the Trump sense of humor. Punching down is Trump’s game.

“No sense of humor,” Hinchcliffe wrote on X Sunday, referring to intolerant Democrats making a fuss about his comedy. By then the Republicans weren’t laughing, either — not with the Latino vote suddenly destabilized, in a matter of seconds, by an ordinary insult comedian punching down at “garbage” Puerto Rico, which was of course a joke, not to be taken seriously. As Hinchcliffe asserted: “I love Puerto Rico and vacation there.”

Also on Sunday, Hinchcliffe reposted a YouTube link featuring the late, arguably great insult comic Don Rickles doing a quick 1984 set at the second Reagan inaugural. The implication behind the post was clear: Why could that guy get away with the stuff I want to get away with? Where did that America go?

The Reagan inaugural Rickles performance amounts to minor, gun-for-hire, far-from-prime insult comedy. It’s a far cry from his anarchic “Tonight Show” appearances in the Johnny Carson years. Those became the stuff of late-night legend. The 1976 Carson show with Rickles butting in on leisure-suited special guest Frank Sinatra, soon to weather a barrage of post-“Godfather” mafioso jokes no one would call daisy fresh, showcased a master of rapid-fire comic malignancy, kidding but a little toxic nonetheless. And yes, dated. And offensive to many, then and especially now. Comedy is like that. Most of it comes and goes, if it even works the first time.

Mr. Warmth: That was Rickles’ nickname. And even past his prime, as his tone and his multidirectional disdain soured, he was 10 times funnier than the insult comic at the top of the Trump rally Sunday.

Audiences can tell a comic almost everything that comic needs to hear in order to tighten, sharpen and put over a few minutes of material. The night before the big rally, Hinchcliffe assumed his comedy club audience was lying, or missing the point. So he tried the garbage line again on Sunday. And it denigrated a substantial voting bloc in a momentous election. It tarnished the low, proud, shameless tradition of insult comedy, simply by being worthless and mirth-free. As a bonus, it may well end up redirecting the course of that election, in ways difficult but not impossible to verify.

As Mr. Warmth might’ve put it, this makes Tony Hinchcliffe one of two things, depending on how you vote.

He’s a hero.

Or he’s a hockey puck.

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(Michael Phillips is the Chicago Tribune film critic.)

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