A comedian giving both campaigns a crisis on the last Sunday before a presidential election was the last thing most people anticipated. But that’s basically what happened on October 27, 2024, when Tony Hinchcliffe performed at Madison Square Garden, one of the world’s most renowned arenas, in Donald Trump’s hometown. His set would be replayed, analyzed, and debated for months.
Hinchcliffe had arrived slowly. He was a young man from Youngstown, Ohio, who, according to him, was a class clown. He worked his way up through the lower levels of stand-up until he was able to write jokes for celebrities on Comedy Central Roasts and was employed by Joe Rogan in Austin. By the time MSG debuted, Kill Tony had amassed almost two million YouTube subscribers. It was a live weekly podcast where aspiring comics had 60 seconds to audition before a panel, raw and unfiltered. It wasn’t well-known. It was the kind of celebrity that has significance for a particular and loyal audience.
His largest room by far was the Madison Square Garden appearance. He announced to the audience that it was his fourth performance in the arena while standing there with his arms extended. “There’s literally a floating island of garbage in the middle of the ocean right now,” he said after that. It’s called Puerto Rico, I believe. The audience responded. The nation as a whole responded more forcefully.
The political pile-on that ensued was unique in that it originated simultaneously from both sides. Alexandria Ocasio-Cortez, a Democratic congresswoman with Puerto Rican ancestry, described the remarks as “super upsetting.” Senator Rick Scott, a Republican, stated unequivocally that “the joke bombed for a reason.” It’s not true and it’s not funny.” On the same day, Bad Bunny, who had long avoided politics, uploaded videos supporting Kamala Harris, and Republican Congresswoman Maria Elvira Salazar expressed her “disgust.” Fans were informed by Ricky Martin that “this is what they think of us.” The backlash was noteworthy for its bipartisan nature; it is extremely uncommon for Rick Scott and AOC to denounce a single incident at a political rally in the same news cycle.
| Full Name | Tony Hinchcliffe |
| Date of Birth | June 8, 1984 |
| Hometown | Youngstown, Ohio |
| Based In | Austin, Texas |
| Profession | Stand-up comedian, podcaster, comedy writer |
| Known For | Host of Kill Tony podcast; appearances on Comedy Central Roasts |
| Kill Tony Podcast | Live weekly comedy podcast; 1.89 million YouTube subscribers |
| Career Start | Began working as a writer for Joe Rogan; wrote jokes for Comedy Central Roasts |
| Notable Appearances | Tom Brady Netflix Roast (2024); Trump MSG Rally (October 27, 2024) |
| Trump Rally Controversy | Called Puerto Rico “a floating island of garbage” at Madison Square Garden; made racially offensive jokes about Latinos, Black people, and Jewish Americans |
| Trump Campaign Response | Distanced itself from Hinchcliffe’s remarks; said the jokes were ad-libbed and did not reflect Trump’s views |
| Celebrity Backlash | Bad Bunny, Jennifer Lopez, Ricky Martin, Luis Fonsi, Alexandria Ocasio-Cortez, and Republican lawmakers including Senator Rick Scott and Congresswoman Maria Elvira Salazar |
| Post-Rally Career | Signed a Netflix deal (March 2025) for three Kill Tony specials plus a one-hour standup special |
| First Netflix Special | Filmed at The Comedy Mothership, Austin, Texas; premiered April 7, 2025 |
| Prior Controversy | Used a racial slur against comedian Peng Deng during a 2021 set; refused to apologize |
The Trump campaign was swift. The Puerto Rico line and other offensive remarks were ad-libbed, according to a spokesperson who told CNN that the jokes didn’t represent the president’s or the campaign’s opinions. The campaign had previously reviewed a list of jokes, and those particular remarks weren’t on it. Trump himself told ABC News he didn’t know the comedian and hadn’t heard the remarks. That might have been totally accurate. Additionally, it’s the kind of distance a campaign creates when something quickly veers off course.
Hinchcliffe did not offer an apology. In reality, he never does. In response to the criticism, he said that people should see the entire set, that his detractors lacked a sense of humor, and that he had made fun of everyone. He made the same defense in 2021 after insulting comedian Peng Deng with a racial slur and refusing to take it back. He stated, “I knew that what I had done was not wrong,” at the time. Even though the majority of people don’t agree with that position, it contains a cohesive worldview.
It is truly difficult to reconcile what transpired next with what the conventional narrative suggests ought to occur following such a controversy. Hinchcliffe and Netflix announced a deal in March 2025 for three Kill Tony specials and an hour-long stand-alone film that would be shot at The Comedy Mothership in Austin. April saw the release of the first. When most anticipated a retreat, Netflix, which had previously supported Dave Chappelle’s trans-themed content, appeared unfazed. For his part, Hinchcliffe claimed on Bill Maher’s podcast that he had done the MSG gig to sway voters and attract the president’s attention without receiving payment. Which objective he was using to gauge success is still unknown. However, it is difficult to attribute the career trajectory—from the MSG controversy to the Netflix deal in less than six months—to chance or coincidence. There’s a feeling, at least in comedy, that no one publicly agrees to the rules governing what creates consequences and what creates a contract.
