Tony Hinchcliffe was a relative unknown to the world of politics before he told a series of off-color jokes about Puerto Rico and Latinos at former President Trump’s Madison Square Garden rally last weekend.

An insult comic best known for brutal roasts and searing personal attacks, Hinchcliffe’s joke referring to Puerto Rico as a floating island of “garbage” landed him at the center of a days-long controversy.

Political observers and entertainment industry experts say Hinchcliffe’s high-profile, controversial routine at the Trump rally, and the backlash it sparked, is likely to have a lasting impact on his career regardless of whether it makes a difference on Election Day.

“I think ultimately it’s great for him,” said Matt Sienkiewicz, chair of the Boston College communication department, who specializes in right-wing comedy. “The economy for a comedian is attention. He introduced himself to a large amount of people. And the fact that somebody who never knew you does not like you is never a harm for a comedian.”

A native of Ohio who got his start at open mic nights and comedy clubs across Los Angeles, Hinchcliffe specializes in insult stand-up, often roasting audience members and other comedians he performs with. He does not market himself as a political or conservative comic, notwithstanding the appearance at the Trump rally.

Hinchcliffe has during interviews cited leading roast comic Jeff Ross as a mentor, and today hosts a popular and raunchy podcast titled “Kill Tony.”

Hinchcliffe’s comedy targeting ethnic groups has stirred controversy and grabbed headlines in the past. He referred to an Asian comic who introduced him one night in May 2021 in Austin using a slur about Asians, sparking criticism.

A no-holds-barred shock artist, Hinchcliffe got a major break earlier this year when he was asked to participate in a live roast of former NFL star Tom Brady, a widely watched event broadcast live on Netflix.

But even a live set for a major comedy provider like Netflix could not compare to the national media boost that comes with making waves at a “MAGA gig,” followers of up-and-coming comics told The Hill this week.

Comedy writers say Hinchcliffe did what he does when he took the stage at Madison Square Garden. The problem was that it was in the context of a political rally and not a comedy club.

“His stuff would have absolutely landed better in a different environment,” said Jim Mendrinos, a comedy writer, producer and teacher at Gotham Writers Workshop in New York. “He’s not the villain, they are. I’m not defending what he said, but what he said in a comedy club or in a special is going to be taken vastly different than a political rally.”

Jon Stewart, one of the biggest names in political satire, on Monday seemed to defend Hinchcliffe, though he also suggested Trump’s Madison Square Garden rally was not the best venue for his style of comedy.

“There’s something wrong with me — I find that guy very funny,” Stewart told his audience. “Now, obviously, in retrospect, having a roast comedian come to a political rally a week before Election Day and roasting a key demographic, probably not the best decision politically.”

The Trump campaign almost immediately distanced itself from Hinchcliffe’s joke about Puerto Rico. The anti-Trump website The Bulwark reported this week Trump’s campaign reviewed Hinchcliffe’s script before he performed at the rally and asked that he remove some jokes from his set.

The line about Puerto Rico was ad-libbed, a campaign source told the outlet.

“I don’t know anything about the comedian,” Trump told reporters Thursday. “I don’t know who he is. I’ve never seen him. I heard he made a statement, but it was just a statement that he made. He’s a comedian, what can I tell you? I know nothing about him.”

A representative for Hinchcliffe did not respond to a request for an interview from The Hill this week, but the comedian defended his work at the rally in a social media post as he was being widely condemned.

“These people have no sense of humor,” Hinchcliffe wrote on the social platform X in response to Minnesota Gov. Tim Walz, the Democratic vice presidential candidate.

Walz had criticized the comedian’s routine, calling him an “ass—-.”

“Wild that a vice-presidential candidate would take time out of his ‘busy schedule’ to analyze a joke taken out of context to make it seem racist,” Hinchcliffe said. “I love Puerto Rico and vacation there. I made fun of everyone…watch the whole set. I’m a comedian Tim…might be time to change your tampon.”

Hinchcliffe’s set sparked more political waves when President Biden on Tuesday sought to criticize him, but ended up sounding like he was calling Trump supporters garbage. As the White House argued Biden’s words were taken out of context, Harris sought to clean up the mess and Trump did a photo op in a garbage truck.

The popular podcaster Joe Rogan, who also dabbles in stand-up comedy and recently hosted Trump for a three-hour friendly interview, said he would have advised Hinchcliffe against the Puerto Rico joke, given the setting.

“It’s just a bad environment for comedy,” Rogan said of the rally on his show. “I would have told him don’t you … dare do that joke. And when I heard he did I went, ‘Oh here we go.'”

Those familiar with Hinchcliffe’s work say they weren’t surprised by the content of the Puerto Rico joke, though delivering it at Madison Square Garden was the wrong call.

“If you’re hiring Tony Hinchcliffe … this is what you’re expecting,” Jordan Klepper, a left-leaning comedian and co-host of “The Daily Show” said during an appearance on MSNBC. “It’s not as if everyone is shocked Hulk Hogan ripped his shirt off, that’s what he does. What’s shocking is that this was at MSG, and it said Trump-Vance in front of him.”

Beyond the political storm, it remains an open question how the episode will ultimately affect the trajectory of Hinchcliffe’s career at the mic.

“The biggest thing is now a lot more people know who he is,” Sienkiewicz said. “In the long run, having told a joke that offended some people is rarely something that brings down a comedian. In all likelihood, the more the controversy, the more people are appalled, the bigger the benefit for him.”