Trump, Hardly New York’s Favorite Son, Brings His Message to Long Island

Donald J. Trump’s rally in Nassau County on Wednesday is another sign of the area’s shift to the right, but some question his choice to spend time in a non-battleground state.

The New York City suburbs are not exactly the definition of a Republican stronghold, so on the eve of a rare campaign rally there, former President Donald J. Trump tried out an unorthodox pitch.

Inflation, he wrote on his social media platform, is “eating your hearts out.” Hundreds of thousands of migrants are flocking to the state while New Yorkers “are fleeing” for less expensive alternatives, he said. Put him in office, Mr. Trump added, and he would even restore the lucrative state and local tax deduction he capped as president.

“What the hell,” Mr. Trump wrote in all capital letters, “do you have to lose?”

Call it hubris or political cunning or an old-fashioned fantasy by a son of Queens, but Mr. Trump’s decision to expend one of the 49 days left in the race rallying at the Nassau Coliseum on Long Island on Wednesday has left political strategists in both parties slightly confused.

To wit: The last Republican to carry New York was Ronald Reagan. Mr. Trump’s own campaign is not meaningfully spending in the state. And despite Mr. Trump’s insistence that he has a “real chance” of winning, recent polls have shown him no closer than 14 percentage points behind Vice President Kamala Harris.

Democrats are happy to watch him while away precious days anywhere but in battlegrounds like Pennsylvania and North Carolina.

“Listen, he could spend every day in this state, and I’ll be happy,” said Jay Jacobs, the chairman of New York’s Democratic Party.

Yet in many ways, the detour to New York offers an ideal backdrop for the issues animating Mr. Trump’s campaign, and nowhere more so than Long Island, the diverse patchwork of suburbs and bedroom communities that juts eastward from New York City.

The region, already one of the most expensive places to live in the world, is suffering under punishingly high housing costs and the toll of inflation. Crime rates have receded since the pandemic-era bump, but some residents report that they still do not feel safe. And many suburbanites have watched in frustration as the city and state have struggled to absorb an influx of more than 200,000 asylum seekers in about two years.

“The fact that he’s coming may seem like a surprise to some people, but there is something going on, a movement going on here,” said Bruce Blakeman, who rode a wave of Republican support to become Nassau’s county executive in 2021. A year later, Republicans won all four House races on Long Island.

Mr. Blakeman has subsequently turned Nassau County into a kind of laboratory for Trumpism, even recruiting an armed force of citizen “special deputies,” and he predicted that the area would warmly welcome Mr. Trump.

Organizers said they ran out of tickets over the weekend for the evening rally. Local Republican leaders are printing custom-made “Nassau ❤️ Trump” and “Suffolk ❤️ Trump” T-shirts for volunteers.

Local Republicans are promising to make the travel worth Mr. Trump’s while. Joseph G. Cairo Jr., the chairman of Nassau County’s storied Republican political machine, has organized a high-dollar fund-raiser on the sidelines of Wednesday’s rally that is expected to net several million dollars.

An invitation obtained by The New York Times offered tickets priced at $5,000 for reserved rally seating and $30,000 for a photo with the former president. For $250,000, the deep-pocketed few could enjoy the “V.I.P. Experience”: a brief chance to meet Mr. Trump, take a photo with him and lock down a “premium seat.” (Tickets for general admission were free.)

For all the enthusiasm, prominent Republicans seem to share little of Mr. Trump’s optimism that he can actually win New York.

“Winning the state of New York is uphill,” said Alfonse D’Amato, a former Republican senator from Long Island who is supporting Mr. Trump despite misgivings. “OK, I’m being generous.”

They are more hopeful, however, that Mr. Trump’s presence will help galvanize the party’s base in crucial down-ballot races. New York is home to perhaps the most important House battleground in the country, and a total of four swing races, nearly enough to tip national control, will play out on Long Island.

The most vulnerable Republican incumbent, Representative Anthony D’Esposito, is slated to speak Wednesday night before Mr. Trump, and signaled on Tuesday that he was eager to talk about Mr. Trump’s revised position on the state and local tax deduction. (Mr. D’Esposito’s spokesman did not respond to requests for comment.)

Mr. D’Esposito’s speaking role carries some risk. He represents a district Mr. Trump lost by 14 points in 2020, and Democrats believe the former president’s visit could motivate their supporters with equal force.

At least three other Republicans fighting to hold onto New York swing seats this fall are steering clear of the event altogether.

Representatives Mike Lawler and Marc Molinaro, both first-term congressmen from the Hudson Valley, said they planned to stay in Washington. Taylor Weyeneth, a spokesman for Representative Brandon Williams of Syracuse, went a step further, clarifying that even “if we weren’t in session, we’d be in our district speaking with constituents.”

Democrats are organizing their own rally outside the Coliseum in protest, featuring members of Nassau County’s sizable Haitian American community. Carrié Solages, a local legislator planning the event, said he expected hundreds of people to turn up who have been horrified to see the president and his allies amplifying outlandish, unfounded claims that Haitian migrants in Ohio were stealing and eating pets.

“We are sick and tired of the Haitian hate,” he said. “It has a significant effect in terms of psychological impact.”

Mr. Blakeman said local Republican officials had been discussing a possible Long Island rally with Mr. Trump’s campaign for months.

The former president held a handful of improvised campaign events around the city this spring when his criminal trial in Manhattan otherwise kept him off the campaign trail. He visited a Harlem bodega shaken by a stabbing, shook hands with construction workers and assembled thousands of supporters in the shadow of a beachfront amusement park not far from his old Atlantic City haunts.

Wednesday’s rally was also originally scheduled to coincide with another court date: Mr. Trump’s sentencing, after he was found guilty on all counts of falsifying business records to conceal a sex scandal. But earlier this month, the judge overseeing the Manhattan case postponed it until November.