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

His campaign team didn’t know everything he had to say, according to a campaign aide. So when Hinchcliffe compared Puerto Rico to a garbage dump, Trump’s team was caught off guard and went into damage control, issuing a statement saying Hinchcliffe’s comments on Sunday “do not reflect the views of President Trump or the campaign.”

But the comment about Puerto Rico took on a life of its own, drawing sustained criticism from Democrats and even some of Trump’s Republican allies. The comments largely overshadowed the former president’s desire to end his 2024 campaign with an unprecedented showing at the Garden.

Many 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 who lives in a competitive district, shared on X: “The only thing that was ‘trash’ was a bad comedy set. Stay on message.”

Trump’s campaign gambled that packing Madison Square Garden would generate the kind of media attention that would give his Make America Great Again agenda a boost in 2016. The series of speakers, including Hinchcliffe, aimed to highlight Trump’s advantage with male voters, especially voters. Surveys show young men are changing their ways this year.

Sunday’s event, where 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 prioritizes in this regard. Closing days of elections.

While Trump remains unapologetic about some of his more incendiary statements, including racist comments, some aides worry about alienating key demographic groups so close to election day; Polls show must-win states like Pennsylvania are in perfect competition. Trump was scheduled to host a rally Tuesday in Allentown, Pennsylvania, where he gained support in some predominantly Hispanic neighborhoods from 2016 to 2020.

Some Republicans objected to the idea that the comments would affect the election results and stated that Trump himself did not make this comment about Puerto Rico.

“I think it’s going to kill everyone, but Trump has a unique brand,” said Sarah Chamberlain, CEO of the Main Street Partnership, which supports congressional Republicans.

Still, it’s rare for the Trump campaign to be concerned about words spoken at one of his campaign rallies, often hushed tones and traffic in often dark rhetoric. Beyond calling Puerto Rico a “floating pile of garbage,” Hinchcliffe used a sexually explicit joke to draw attention to illegal immigration, saying Latinos have too many children and mocking a Black man who he said was “carving a watermelon” for Halloween. The joke drew mixed reactions from Trump supporters, many of whom brought their young children. He also targeted Arabs and Jews in his statements.

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

Trump supporters are rarely impressed by his comments. So the vulgar nature of some speakers’ remarks at Madison Square Garden may not matter, said Doug Heye, former communications director for the Republican National Committee. One speaker said Harris was “pimp handlers,” while another called her the Antichrist.

“We keep asking ourselves whether the latest outrage of the day will hurt Trump,” Heye said. “Nine years from now, if we go back to the ‘Access Hollywood’ tape, the obvious answer is no.”

Puerto Ricans are US citizens who can vote if they reside in a US state. A major Republican donor backing Trump’s campaign worried the rally could cost him votes. Many people of Puerto Rican descent live on the U.S. mainland, particularly in Florida and New York, but also in Pennsylvania, where this is particularly concerning, the donor said.

The Harris campaign tried to create a split-screen moment. Before the Trump rally on Sunday, Harris unveiled a plan for Puerto Rico that includes modernizing the island’s energy grid. Puerto Rican rapper and global superstar Bad Bunny shared Harris’ plan on social media.

Harris said Monday that the rally showed Trump was “focused and actually fixated on his grievances, on himself, 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 opponent even within his own party, dismissed the backlash. “To everyone mad at @TonyHinchcliffe — THIS WAS A JOKE!” he wrote to X.

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

Trump’s vice president, Sen. J.D. Vance (R., Ohio), echoed Walz’s remarks. “I think it shows that Kamala Harris’s closing message is actually saying that the people who voted for Donald Trump are all Nazis and that you should be really angry when a comedian makes a joke,” he said.

Trump has used podcasts and other alternative media sources during the 2024 election cycle, particularly because of their mass appeal to young men who promote a kind of “bro” culture built in part on the concept of unapologetic masculinity. Many podcasters have praised Trump, even if figures like Joe Rogan have not openly endorsed him.

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

Dana Mattioli contributed to this article.

Write to Natalie Andrews at [email protected] and Vivian Salama at [email protected].