Donald Trump Could Be His Own ‘October Surprise,’ Analysts Warn

Former President Donald Trump’s silence amid outrage sparked by his Madison Square Garden rally on Sunday may be doing fatal damage to his presidential campaign, according to experts and analysts.
Comedian Tony Hinchcliffe referred to Puerto Rico, a U.S. territory, as a “floating island of garbage” during the New York City event on Sunday, quickly drawing backlash from Latino Americans.
While Trump campaign senior adviser Danielle Alvarez said in a statement that “this joke does not reflect the views of President Trump or the campaign,” the former president himself said only that he did not “know” Hinchcliffe while speaking to ABC News on Tuesday.
Hinchcliffe’s joke and Trump’s failure to fully address it have prompted some to argue that the moment was effectively the Trump campaign’s self-induced “October Surprise”—a term used to describe an event that could change a presidential election’s outcome.
Trump did not address the joke during Tuesday’s press conference at Mar-a-Lago. He will have another opportunity during a Tuesday night rally in Allentown, Pennsylvania, a city that has one of the largest populations of Puerto Ricans in the critical battleground state.
Gustavo Torres, the executive director of Latino advocacy group CASA, told Newsweek in a call with national Latino leaders on Tuesday that Trump’s rally would not win him back any votes that he may have lost over the Puerto Rico remarks.
“He needs to apologize to the Puerto Rican community, to the Latino community, and he’s not doing that,” Torres said. “Even if he apologizes, I guarantee you that the Puerto Rican community, our members in Pennsylvania and in Georgia, are never going to forget.”
“I believe that that was the October Surprise for the Latino community,” he added. “That is the October Surprise for the Puerto Rican community. And we are going to communicate that every single day from now until November 5.”
Political analyst Craig Agranoff told Newsweek that the “negative feedback” Trump is receiving regarding the New York rally was “‘significant” and could represent a “turning point” just one week before Election Day.
“Given the timing, this backlash could indeed turn into an ‘October surprise,” Agranoff said. “The rally’s polarizing effect may mobilize his critics just as much as his supporters, leading to a sharp public reaction. Whether this event becomes a turning point depends on how it’s managed in the coming weeks.”
“If the negative feedback grows, it could shift focus onto his more controversial aspects, potentially impacting his broader appeal heading into the final stretch of the campaign,” he added.
Archbishop of San Juan de Puerto Rico Roberto González demanded on Monday that Trump apologize “personally” for allowing Hinchcliffe to make the joke at his rally. Ángel Cintrón, the chair of Puerto Rico’s Republican Party, has said he will not vote for Trump without an apology.
Political analyst Larry Sabato said during a Tuesday CNN appearance that he did not expect Trump to apologize since the ex-president “never apologizes for anything.” He also referred to the Madison Square Garden rally as a potential “October Surprise.”
“I do think there’s some possibility that Sunday, not just because of the alleged comedian, but also because of the other things that were said and done and things that weren’t said and done—that could be an October Surprise,” said Sabato. “It really could be. It’s having an effect.”
During a CNN appearance on Monday, Geraldo Rivera, a veteran Puerto Rican American journalist and a former friend of Trump, said that he thought the joke would become “famous for ending President Trump’s meteoric campaign to be reelected.”
“I think that the surveys, the polls will show that this was the time, this was the moment where things turned on Donald Trump,” Rivera said. “There is no reason a Latino American should vote for Donald Trump…He has disqualified himself by surrounding himself with hateful, ugly rhetoric.”