Nobody saw Tony Hinchcliffe upending the election. Maybe they should have

Usually, when a comedian bombs at Madison Square Garden, it doesn’t make the front page of The New York Times. It certainly doesn’t shake up the state of play in a dead-heat presidential election right at the finish line. But then again, nothing else about this election has been usual.

On Sunday night, Austin-based comedian Tony Hinchcliffe, whose popularity is enormous but extremely narrow, took the stage during Donald Trump’s homecoming rally at MSG. When it was his turn to speak, he told a series of lewd and racist jokes, including, most notoriously, one whose apparent punchline declares Puerto Rico “literally a floating island of garbage.”

It’s the same flavor of joke Hinchcliffe is known for making on his podcast, Kill Tony, and on stage at Joe Rogan’s “anti-woke” Comedy Mothership in Austin. Because he made this particular joke at a Trump rally, however, the fallout has been heavy—with denunciations from Latin music superstars like Bad Bunny and even GOP politicians like Senator Rick Scott.

How could anyone have seen this coming? How could anyone not have?

Who is Tony Hinchcliffe?

Over the past few months, Trump has done everything possible to court young male voters. Those outreach efforts have taken him to several Ultimate Fighting Championship events, but mainly they’ve involved a Tasmanian Devil–style blitz through podcasts and Twitch streams aimed at feisty young men. Trump’s appearance on Joe Rogan’s show last week marked just the latest stop on a rambling tour of comedian-hosted podcasts like Theo Von’s This Past Weekend and Andrew Schulz’s Flagrant. All of these comics swim in the same “anti-woke” pool as Hinchcliffe and have performed together, so it was only a matter of time before his path also crossed the former president’s. Rogan even suggested on his show two months ago that Hinchcliffe “write bangers” for Trump. Apparently, the message was received.

Although until very recently, Hinchcliffe managed to fly beneath the mainstream radar, he’s been a fixture in the comedy scene for a long time. After first embarking on a career in standup in the late-aughts, he spent years performing at the Comedy Store in Los Angeles. Eventually, he came to Rogan’s attention and the two went on tour together, the opening act absorbing some of his benefactor’s core audience in the process. As a regular in the writers’ room for Comedy Central’s Roasts, he became known for his insults. Fans can now hear him deliver those every week on Kill Tony, the podcast he started in 2013, where comedians perform short sets and Hinchcliffe and his cohosts offer brutal critiques.

With the obvious exception of his massive podcast audience, Hinchcliffe is most familiar to comedy fans from two moments in his career. Most recently, his Tom Brady roast set attracted a lot of attention through provocative jokes like the following: “Kevin [Hart] is so small that when his ancestors picked cotton, they called it deadlifting.” It’s the kind of joke that hovers a quarter-inch above the third rail of racism, designed to induce shock-laughter and offense in equal measure. A few years earlier, though, Hinchcliffe stoked far more offense than shock-laughter when he hurled blatantly racist slurs at fellow comedian Peng Dang at an Austin comedy club. In the ensuing outrage cycle, Hinchcliffe lost an agent at WME—and likely picked up many new fans whose belief in free-speech absolutism supersedes their love of comedy.

Those fans might eat up jokes like Tony Hinchcliffe’s Puerto Rico gambit, jokes rooted not in humor but in flouting common decency, tolerance, and the norms of living in modern society. A lot of other people, however, hate hearing such jokes—either because the jokes violate their personal values or because they too openly celebrate those values to anyone who might be listening. In this case, “anyone who might be listening” happened to include roughly everyone.

Trump’s flirtation with the “anti-woke” comedy podcast world may have been mutually beneficial, but it was by no means a two-way street. Trump can go on a podcast like Theo Von’s or Andrew Schulz’s, say the kinds of controversial things he often says, and possibly win over a niche new audience. When one of those podcasters enters Trumpworld, though, and says the kind of controversial things they often say, it can potentially turn off mass segments of the electorate. Any speaker at a Trump rally is subject to the same intense media scrutiny he is—just without the legion of high-profile backers who never seem to condemn Trump for anything. (Hinchcliffe has reportedly lost at least one lucrative sponsorship deal since his rally appearance.)

Saying the quiet part out loud

Whatever damage Hinchcliffe’s jokes inflicted on his career, if any, the jokes have been far more detrimental to Trump’s campaign. If Hinchcliffe had said the same things to Trump on a podcast, as long as Trump didn’t firmly agree with him, it might not have even generated headlines. However, without the cushioning biome of “anti-woke” podcast expectations, Hinchcliffe’s jokes effectively speak for, and represent, the Trump campaign. It probably wasn’t by accident that the closest thing to an “anti-woke” podcaster at the Republican National Convention was Ted Cruz.

The candidate has spent the past few days trying in vain to distance himself from Hinchcliffe’s jokes, and undo the ire of Puerto Rican voters in swing states like Pennsylvania. It’s dubious to plead ignorance, however, when Team Trump clearly invited Hinchcliffe because his strong stance on free speech overlaps with a campaign theme–and especially when the team reportedly vetted the podcaster’s remarks, going so far as to edit out an offensive word.

The blowback of the past few days is apparently just what happens when the line between MAGA politics and “anti-woke” podcasts is erased, and dog whistles are replaced by screaming slurs through a megaphone. The strange alliance between the two worlds was perhaps always destined to end in spectacular failure. As they continue fighting for absolute freedom of speech, Team Trump and Hinchcliffe would do well to remember they’re technically allowed to say anything they want—they should just be prepared for what happens when the entire world is listening.