While Puerto Ricans cannot vote in general elections despite being US citizens, they can exert a powerful influence with relatives on the mainland.
Phones across the island of 3.2 million people were ringing minutes after the speaker derided the US territory Sunday night, and they still buzzed Monday.
Democratic Vice President Kamala Harris is competing with Trump to win over Puerto Rican communities in Pennsylvania and other swing states.
Shortly after stand-up comic Tony Hinchcliffe said that, "I don't know if you guys know this, but there's literally a floating island of garbage in the middle of the ocean right now. I think it's called Puerto Rico," Puerto Rican reggaeton superstar Bad Bunny announced he was backing Harris.
Hinchcliffe's set also included lewd and racist comments about Latinos, Jews and Black people, all key constituencies in the election.
When he was president, Donald Trump insulted Puerto Ricans and left them behind. We are not going back. — Kamala Harris (@KamalaHarris) pic.twitter.com/2pkMDsSljVOctober 28, 2024
Milagros Serrano, 81, has a son who lives in the swing state of Pennsylvania and said the entire family was outraged by the comedian's comments.
"He can't be talking about Puerto Rico like that," she said.
"He's the one who's a piece of garbage."
Puerto Rico became a US territory in 1917, and the first large wave of migration occurred after World War II to ease labour shortages.
There are now more Puerto Ricans in the US than on the island.
Those who stayed behind say they often feel like second-class citizens because they can't vote in presidential elections and receive limited federal funding compared with US states.
That festering resentment erupted when Trump visited Puerto Rico after Hurricane Maria slammed into the island as a powerful category four storm in 2017.
He tossed paper towels into a crowd and denied the storm's official death toll, with experts estimating that nearly 3000 people died in the sweltering aftermath.
José Acevedo, a 48-year-old health worker from San Juan, shook his head as he recalled the feelings that coursed through him when he watched the Sunday rally.
"What humiliation, what discrimination!" he said early on Monday as he waited to catch a public bus to work.
Acevedo said he immediately texted relatives in New York, including an uncle who is a Republican and had planned to vote for Trump.
"He told me that he was going to have to analyse his decision," Acevedo said, adding that his relatives were in shock.
"They couldn't believe it."
The comments dominated local news sites late into the night and prompted Jenniffer González, Puerto Rico's representative in Congress for the pro-statehood New Progressive Party and a Trump supporter, to call them "despicable, misguided and disgusting."
"They do not represent the values of the GOP," she said.
Politics in Puerto Rico are defined by the island's political status, so it's common to see Democrats and Republicans be members of the same local party.
Hinchcliffe's comments also prompted reaction from Puerto Rican stars including Ricky Martin, who previously endorsed Democratic presidential candidate Kamala Harris.
He posted a video of the crude joke and wrote, "This is what they think of us."
Michael Meléndez Ortiz, a 33-year-old unemployed janitor, said he and a friend thought the video was fake at first because they were so taken aback by what the comedian said.
"We must be respected," he said. "We are good and upstanding people."
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