How the Trump campaign’s gamble on a provocative comic backfired

Donald Trump’s campaign invited Tony Hinchcliffe, who hosts the popular podcast “Kill Tony,” to do a comedy set at the former president’s rally at Madison Square Garden because of the comic’s popularity with young men, particularly after he sold out two shows at the same venue in August.

The campaign didn’t know everything he would say, according to a campaign aide. So when Hinchcliffe likened Puerto Rico to a garbage dump, Trump’s team was caught off guard and jumped into damage control, releasing a statement that Hinchcliffe’s remarks Sunday did “not reflect the views of President Trump or the campaign.”

But the comment about Puerto Rico has taken on a life of its own, receiving sustained criticism from Democrats and even some Republican allies of Trump. The comments largely overshadowed the former president’s desire to wind down his 2024 campaign with an unrivaled spectacle at the Garden.

Several GOP members of Congress running for re-election said the comments were a distraction. Rep. Anthony D’Esposito, a New York Republican and Puerto Rican in a competitive district, posted on X: “The only thing that’s ‘garbage’ was a bad comedy set. Stay on message.”

Trump’s campaign gambled that filling up Madison Square Garden would create the kind of media attention that gave his Make America Great Again agenda a signal boost in 2016. The lineup of speakers, including Hinchcliffe, was meant to press Trump’s advantage with male voters, particularly the younger men who polls suggest have shifted his way this year.

Sunday’s event—during which some speakers including Hinchcliffe at times made racist, sexist or otherwise derogatory comments about Vice President Kamala Harris, Democrats, and immigrants—illustrates Trump’s enduring struggle to appeal to the political center, something his opponent has made a priority in the closing days of the election.

While Trump has been unapologetic about some of his more incendiary remarks, including racist comments, some of his aides are worried about alienating important demographic groups so close to Election Day, with polling showing must-win states such as Pennsylvania in a dead heat. Trump was set to host a rally Tuesday in Allentown, Pa., an area where he gained support in some heavily Hispanic neighborhoods from 2016 to 2020.

Some Republicans pushed back on the idea that the comments would affect the election results, saying that Trump himself didn’t say the remark about Puerto Rico.

“I think it would kill anyone else—but Trump has a unique brand,” said Sarah Chamberlain, the CEO of Main Street Partnership, which supports congressional Republicans.

Still, it is rare for the Trump campaign to show concern over words spoken at one of campaign’s rallies, which are usually raucous and often traffic in dark rhetoric. Beyond calling Puerto Rico a “floating pile of garbage,” Hinchcliffe said that Latinos have many children, using a sexually explicit joke to make a point about illegal migration, and mocked a Black man whom he said “carved watermelons” for Halloween. The joke received mixed responses from the crowd of Trump supporters, many of whom brought their young children. He also targeted Arabs and Jews in his remarks.

Hinchcliffe defended his set, posting on X: “These people have no sense of humor…I love Puerto Rico and vacation there. I made fun of everyone…watch the whole set.”

Trump supporters are rarely fazed by his comments. For that reason, the crude nature of the remarks by some speakers at Madison Square Garden might not matter, said Doug Heye, a former communications director for the Republican National Committee. One speaker said Harris had “pimp handlers” and another called her the Antichrist.

“We keep asking ourselves if the latest outrage du jour will hurt Trump,” Heye said. “Nine years into this, going back to the ‘Access Hollywood’ tape, the glaring answer is no.”

Puerto Ricans are U.S. citizens who can vote if they have residency in a U.S. state. One top Republican donor supporting Trump’s campaign worried the rally could cost him votes. Many people of Puerto Rican descent live in the U.S. mainland, particularly in Florida and New York, but also in the swing state of Pennsylvania, which the donor said was particularly concerning.

The Harris campaign sought to make a split-screen moment. On Sunday before the Trump rally, Harris rolled out a plan for Puerto Rico that included modernizing the island’s energy grid. Puerto Rican rapper and global superstar Bad Bunny shared Harris’s plan on social media.

Harris said Monday that the rally showed that Trump “is focused and actually fixated on his grievances, on himself and on dividing our country.”

Sen. Rick Scott (R., Fla.), a close Trump ally, said the “joke bombed for a reason. It’s not funny and it’s not true.” Rep. Matt Gaetz (R., Fla.), a frequent contrarian even within his own party, dismissed the backlash. “To everyone mad at @TonyHinchcliffe—IT WAS A JOKE!” he wrote on X.

Sen. Marco Rubio (R., Fla.) and other Trump allies said that while Hinchcliffe’s remarks were in poor taste, so were those made by Democrats, including Harris running-mate Gov. Tim Walz, who likened the Trump rally Sunday to one held in the city by Nazi supporters in 1939. “There’s a direct parallel to a big rally that happened in the mid 1930s at Madison Square Garden,” Walz said Sunday in Las Vegas. “And don’t think that he doesn’t know for one second exactly what they’re doing there.”

Sen. JD Vance (R., Ohio), Trump’s running mate, seized on the Walz remarks. “I think that it’s telling that Kamala Harris’s closing message is essentially that all of Donald Trump’s voters are Nazis and you should get really pissed off about a comedian telling a joke,” he said.

Trump has taken to podcasts and other alternative-media sources in the 2024 election cycle given their mass appeal, especially with young men who promote a type of “bro” culture built, in part, on a concept of unapologetic masculinity. Many of the podcasters, such as Joe Rogan, have praised Trump, even without explicitly endorsing him.

Rogan suggested on his podcast last summer that Trump should hire Hinchcliffe and other comics “to just tour with him, and just write one-liners.”

Dana Mattioli contributed to this article.

Write to Natalie Andrews at natalie.andrews@wsj.com and Vivian Salama at vivian.salama@wsj.com