MASSAPEQUA PARK, N.Y. — Just to the right of the register at Village Wines & Spirits, a bottle of Virginia chardonnay bore a label that suggested that it was best paired with Republicans: It was from Trump Winery.
“Some people love it and want to take a picture with it and take it home,” one of the shop’s owners, Eric Kaczmarski, said. “For some customers, it’s just triggering.”
The polarizing reactions in this New York City suburb are understandable: Although Democrats now slightly outnumber Republicans on Long Island, the area still retains its conservative roots, especially out east.
In Suffolk County, the Republican incumbent, Representative Lee Zeldin, is an ardent supporter of the Trump administration; the district just to the west is held by Peter T. King, a 14-term Republican who counts himself among the president’s closer friends.
But Democratic leaders believe that this November’s election may present a rare opportunity for them to seize one or both of the House seats. The two contests are on the Democratic Congressional Campaign Committee’s Red to Blue program, with Democrats pointing to three factors that could lead to possible victory: President Trump’s deepening unpopularity; the growing number of Democrats in the area; and the fact that Mr. King, the longest-serving Republican in New York’s congressional delegation, is not seeking re-election.
“I do think that to some extent these candidates’ fortunes rise and fall with the president,” said Chapin D. Fay, a Republican strategist who ran Mr. Zeldin’s 2014 congressional primary campaign, but is no longer involved.
“This is going to be a referendum on Trump,” he added. For the Democrats on Long Island, “That is the strategy they’re left with,” he said, “and it may work if the poll numbers are accurate and they get worse.”
The challenge for Mr. Zeldin and, to a lesser extent, Andrew Garbarino, a Republican state assemblyman vying to succeed Mr. King, is to gauge how much they should tether their campaigns to Mr. Trump before doing so becomes a liability.
Registered active Republican voters outnumber Democrats by roughly 5,000 in Mr. Zeldin’s district, where processions of trucks flying Trump banners could be seen heading down Montauk Highway on many recent weekends. Suffolk County voters favored Mr. Trump over Hillary Clinton in 2016 by a nearly eight-point margin.
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Mr. Zeldin has also won much of the credit for drawing the president’s attention to the area’s gang crisis — dozens of murders by MS-13, a Los Angeles and Central American crime group — and helping wrangle federal assistance to combat the problem.
Mr. Zeldin has leveraged his loyalty to the president into a campaign studded with celebrity presences from Mr. Trump’s orbit: Karen Pence, the wife of Vice President Mike Pence, was the marquee guest this month at a virtual fund-raiser for Mr. Zeldin; last year, Donald Trump Jr. hosted a North Shore fund-raiser for him.
There are benefits to being in Mr. Trump’s circle: As of Sept. 30, Mr. Zeldin had raked in nearly $7 million in financial donations to the roughly $4.6 million raised by his opponent, Nancy Goroff, a chemist and a professor at Stony Brook University, according to Federal Election Commission filings. Mr. Zeldin has roughly $2 million cash on hand, Ms. Goroff less than half a million dollars.
But Mr. Zeldin is also aware of the evolving loyalties of the district; two years ago, he won re-election by only four percentage points over Perry Gershon, a Democratic political newcomer.
Mindful of Mr. Trump’s polarizing effect, Republican leaders are careful to point out where daylight exists between the congressman and president. Although Mr. Zeldin was considered the second most conservative Congress member from New York by the political website govtrack.us, his supporters note he is ranked the 12th most bipartisan Congress member by the Lugar Center and Georgetown University’s McCourt School’s Bipartisan Index Rankings.
“I have been willing to work with anyone to find common ground however possible,” Mr. Zeldin wrote in an email in response to a question about the potential risk of aligning closely with Mr. Trump.
Many Republican leaders, like Jesse Garcia, the chairman of the Suffolk County Republican Committee, frame Mr. Zeldin’s loyalty to the president as an asset, not a liability.
“Lee Zeldin has effectively used relationships with the White House, no matter who occupies it, to deliver for his district,” Mr. Garcia said. “When he agrees with the president, he will say so; when he disagrees with the president, he will say so.”
That message has resonated with Franklin Robinson, a housekeeper at a nursing home who is from Riverhead. Mr. Robinson, 41, said that because of his disgust for Trump’s behavior, he plans to vote for Joseph R. Biden Jr. for president; yet he still supports Mr. Zeldin for Congress. “I see it as he did what he had to do, to do a good job,” Mr. Robinson said of the congressman.
Even Ms. Goroff, who defeated Mr. Gershon in the June primary, seemed to recognize that running a staunch anti-Trump campaign might not make the most sense in Suffolk County.
She has leaned heavily on her science credentials in the pandemic climate, while some of her television ads have denounced the connection between her opponent and the president.
“Our focus has really been on the benefits of science at the table,” Ms. Goroff said in an interview. “Now with the pandemic, I think it has crystallized it for so many people. There are lots of people who supported Trump and Zeldin in the past, and voted for them in the past, and now they are wearing masks everywhere they go.”
Democratic strategists say it was understandable why Ms. Goroff might be reluctant to alienate potential Republican voters by aggressively attacking the president. “There is probably a smaller group of people that are true undecided and persuadable for both sides, and that’s always where you win,” said Keith Davies, the spokesman for the Suffolk County Democratic Committee. “I think threading that needle is important, even more so than in years past.”
Treading gently between parties is perhaps even more essential to win the neighboring congressional seat being vacated by Mr. King, who is retiring after 28 years in the House, and who has endorsed Mr. Garbarino as his replacement.
In recent years, Mr. King’s re-election margins have slimmed to single digits as the district’s demographics and geographic borders have changed. Minorities make up more than a quarter of Nassau residents, according to the United States census, and a third of the district is now in Nassau County, where the Democratic shift led to the upset in 2018 of three Republican state senators, delivering the State Senate to Democratic control for the first time in a decade.
In an interview, Mr. Garbarino, who is running on a law-and-order platform, pointed out that he sided with the Democrats in his frustration with president’s decision to cap state and local taxes, or SALT. “Long Island has always been a split ticket voter; they vote for the person, they don’t just vote for the party,” Mr. Garbarino said.
Seeing an opportunity, Democratic supporters and outside groups have poured cash into the race. The Democratic opponent, Jackie Gordon, a public-school teacher and a 29-year veteran of the Army Reserve who served in the Iraq war, has vastly outraised Mr. Garbarino with over $3. million to his opponent’s approximately $1.4 million.
Still more outside funding has poured into the race, including over $3 million dedicated to opposing Mr. Garbarino, who has about $400,000 cash on hand, while his competitor has over $577,000.
Ms. Gordon, an immigrant from Jamaica, is not taking any chances, publicly praising Mr. King’s record while identifying as a moderate. Seen by some as representing the changing demographics of the island, Ms. Gordon and her team remain keenly aware of the dual ideologies of Long Island voters.
In her campaign ads, Ms. Gordon highlights her Jamaican roots and her background in the military and in the schools.
“I’ve been to basic, and I’ve taught yoga,” Ms. Gordon says in one ad showing pictures of her dressed in fatigues in basic training, and then in a yoga pose. But the ads stay clear of criticizing Mr. Trump, which comports with her campaign image of being someone who can bridge political differences.
“I think we need representatives who are willing to want to bring us together from the onset,” Ms. Gordon said in an interview. “That is who I am innately.”