Can Lee Zeldin Reinvent His Way to the NY Governor’s Mansion?

SHIRLEY, N.Y. — As a young U.S. Army lawyer of unmistakable ambition, Lee Zeldin could almost see his future unfurling before him. It was his first stint in Iraq, and he was already imagining the kind of distinguished career in uniform that would have laid the groundwork for one in politics.

Then a Red Cross message arrived on the base where Mr. Zeldin was embedded as a captain with the 82nd Airborne Division. His girlfriend had gone into dangerously premature labor with twin girls. Doctors were not optimistic about the babies’ survival. His commanding officer sent him home to mourn.

“This I vividly remember the emotion of,” Mr. Zeldin, now a conservative congressman, recalled in a recent interview. “My priorities became all about my daughters.”

The girls survived after months in the hospital. But rather than returning to Iraq, Mr. Zeldin took a desk job back at Fort Bragg in North Carolina, got married and then was discharged. At just 27, he found that the life he had imagined had veered off course.

It was not the first time, nor the last. As a high school senior here on the South Shore of Long Island, Mr. Zeldin sought a prestigious appointment to West Point, only to fall short. After leaving the Army in 2007, he almost immediately entered a race for Congress, hoping to jump-start his political career. He lost in a blowout.

But in every case, Mr. Zeldin has shown aptitude for finding a quick path to reinvention that has helped fuel his political ascent. Now, at age 42, it has put him closer than any Republican since George E. Pataki two decades ago to one of the nation’s most influential political posts, the governorship of New York.

Though Gov. Kathy Hochul, the Democratic incumbent, remains the front-runner, Mr. Zeldin’s late surge in the polls has shocked even political strategists and sent Democrats scrambling to prop up their candidate. With Ms. Hochul’s huge war chest and a vast Democratic registration advantage, few expected Mr. Zeldin to come close to winning, and perhaps with good reason: He does not easily fit the profile of a New York power player.

In a state shaped by wealthy business interests and often governed by larger-than-life personalities and family dynasties, Mr. Zeldin is an outlier. He grew up in law enforcement households of modest means. He can be introverted and awkward with voters. And in a state dominated by the political left, he is probably the most conservative serious contender for the governorship in modern memory — even voting to overturn the 2020 election on Jan. 6, 2021.

Yet a careful review of his public and private life, including two dozen interviews with family, friends, colleagues and critics, shows that Mr. Zeldin’s emergence as a political force stems from decades of meticulous planning, comfort with taking risks, well-timed alliances with more powerful Republicans and, above all, a knack honed from a young age for what allies call adaptation but his critics view as a more cynical political shape-shifting.

Those qualities have been on full display in this fall’s campaign, as Mr. Zeldin moved swiftly to tap into two powerful currents of discontent that Democrats appear to have misjudged and that threaten to scramble the state’s usual political order: painful inflation eroding New Yorkers’ sense of financial well-being and fears about rising crime.

“He’s grabbed the right issues and hasn’t let go,” said Rob Astorino, who lost to Mr. Zeldin in this year’s Republican primary.

But his instincts have also been evident as he tries to execute another on-the-fly transformation, playing down hard-line positions that served him well while he climbed the Republican ranks in Albany and Washington but are now politically inconvenient, while offering scant details on some of his latest policy proposals.

Among them are fights to limit abortion rights and gun control, and votes against legalizing same-sex marriage and in favor of eliminating the Affordable Care Act — all in conflict with most New Yorkers’ views. And though most days Mr. Zeldin avoids public mentions of former President Donald J. Trump, he was until recently one of Mr. Trump’s most vocal defenders, a fact that Democrats have driven home in millions of dollars of ads.

“He comes across as your mildly opinionated next-door neighbor,” said Tim Bishop, a former Democratic congressman who defeated Mr. Zeldin in 2008 but lost to him six years later. “But debate him — be on the receiving end of some poison-pen-type emails and postings — and that’s not who he is.”

For many New Yorkers, the South Shore of Long Island evokes images of sand, summer and the superrich. That has almost nothing to do with Shirley, the working-class hamlet where Lee Michael Zeldin grew up and that left a clear imprint on his social and political worldview.

It was a predominantly white town of cops, small-business owners and nurses trying to make it on the outskirts of New York City’s suburban sprawl — the kind of voters Mr. Zeldin channels in his campaign.

“Nobody was wealthy. Nobody had already made it,” Mr. Zeldin said. “Every single person, whatever they were going to achieve in life, they were going to have to earn.”

His own family, which was Jewish, was no exception. After his parents’ early divorce, Mr. Zeldin’s home life was cleaved in two. His mother, a teacher, remarried a state trooper. His father was a fraud investigator and private detective who graduated from the New York Military Academy, Mr. Trump’s alma mater, and later married a Nassau County probation officer.

At William Floyd High School, Mr. Zeldin stood apart and sometimes alone. When other students got high or in fights, former classmates said, he was busy taking college-level courses and playing varsity tennis and running track.

“Lee was driven in a direction to where he is now, he stayed out of trouble,” said Frank Kazanecki, a classmate. “There was plenty of trouble if you wanted it. I’m not going to say it’s a rough school, because there are rougher out there, but in terms of the Island, the area doesn’t have a great reputation.”

In 10th grade, Mr. Zeldin joined Youth and Government, recalling in the interview that his motivation was “to pick up girls.” He got hooked on politics instead. He was voted best debater by the statewide group and later served as lieutenant governor on an annual trip to mock legislate on the floor of the State Capitol.

“There was no doubt,” said Spencer Gaines, an uncle. “He had ambitions.”

After the appointment to West Point fell through, he returned to Albany to attend college at the state university in August 1998 and wasted little time setting a course that might get him back to the Capitol for real. He signed up for R.O.T.C., began working in the office of a Republican state senator, Kenneth LaValle, and was elected president of the campus Republicans.

Mr. Zeldin began law school, at the Army’s expense, just days before two planes flew into the World Trade Center, and passed the bar at 23, making him the state’s youngest lawyer at the time. By 2005, with two wars underway in the Middle East, he was stationed at Fort Bragg.

‘Lee had a plan’

Since his first campaign, Mr. Zeldin has put his military service at the center of his pre-politics biography. He stresses that he served on “the front lines” in Iraq with fellow paratroopers, leveraging the reputation of the Army’s famed 82nd Airborne Division.

The job was far from glamorous. Though Mr. Zeldin says he did parachute from a plane 18 times in training, as part of the Judge Advocate General’s Corps, he spent much of his early military career in law offices working on tax returns, family disputes and courts-martial. “Used car sales scams, near-usurious interest rate deals and threatening bill collectors became his passion,” one superior wrote in a 2005 performance evaluation.

His stint overseas was not quite two months in the summer of 2006.

In the interview, Mr. Zeldin described it as a “CSI: Miami-type mission” in which he provided legal advice to a detainee operations mission during a brutal stretch of the conflict. Given the mission’s secretive nature, it was difficult to independently corroborate details.

“My commander operated under the belief that everyone in the battalion should be participating in every mission, so I was in full gear kicking out doors and on foot patrols,” he said.

In September, when his girlfriend went into labor at just 22 weeks, Mr. Zeldin raced back to Washington. He married her the following January in North Carolina, and the couple decided he would have to move to the Army Reserves.

“It was a drastic, sudden shift,” Mr. Zeldin said.

But even before then, he had a political future in mind.

“Lee had a plan,” said Cory Simpson, who lived with him near Fort Bragg. “He was always going to do politics. That was very, very clear.”

Mr. Simpson recalled that at their shared house, Mr. Zeldin became a poker maven and learned to count cards in blackjack. He played video games and the piano, and delighted in pushing boundaries with his humor.

Mr. Zeldin said in the interview that he closed the door on politics after college for a career in uniform. But Mr. Simpson, who later ran for Congress himself, remembered that at home at night, serving in elected office never seemed far from his roommate’s mind.

“He was thinking about and iterating on opportunities and races and numbers and what percent win and that stuff,” Mr. Simpson said.

Indeed, almost a year to the day after his daughters’ birth, Mr. Zeldin filed paperwork to run for Congress back home in Shirley, where he had returned to live with his wife, Diana Zeldin, who is Mormon and now works at a law firm.

‘Ahead of his time’

In a state where power is often built around the political clubhouse and oversize personalities, Mr. Zeldin has always operated as an aloof — if opinionated — outsider.

“He was not a socializer, not a cocktail circle guy,” said Chapin Fay, a former aide. “Every time I was with him in Albany, he would go back to the hotel after session, he’d get a binder from staff filled with news clips, issues research, legislation, and he’d study.”

After Mr. Zeldin lost by 16 points to Mr. Bishop in 2008, Republicans — including Kevin McCarthy, the future House Republican leader — advised him to lower his sights and build up more methodically. He poured himself into a small law practice, and two years later, with the midterm tide moving in Republicans’ favor, Mr. Zeldin flipped a State Senate seat, harnessing outrage over a Metropolitan Transportation Authority payroll tax in a way that would foreshadow his intense focus on crime in the present race.

In Albany, he allied himself with Dean Skelos, a fellow Long Islander and more moderate Republican who led the Senate. The proximity to power helped him deliver on promises to curtail the transit authority tax and fund a landmark program for veterans dealing with post-traumatic stress disorder and brain injuries.

In private, he was already discussing the possibility of a statewide run, and in public, he poked fun at his own ambition. During the Legislative Correspondents’ Association’s 2013 roast, he parodied Billy Joel’s “Piano Man”: “Sing me a song, I’m a senator. Sing me a song tonight. Cause someday I might be a congressman, if I get enough votes from the right.”

“He was a perfectly pleasant, polite young man,” said State Senator Liz Krueger, a liberal Democrat, who described Mr. Zeldin as a backbencher. “He seems to have drank the MAGA Kool-Aid after he left us and just become more and more of a zealous right-winger.”

His conservative views were already evident, though. In 2011, he voted against legalizing same-sex marriage and in 2013, in the aftermath of the Sandy Hook Elementary School shooting, opposed a new law expanding the state’s assault weapons ban.

Those views spilled over into a 2014 rematch with Mr. Bishop in a district that had been steadily shifting rightward during the Obama years. This time, Mr. Zeldin vowed to repeal Obamacare and warned that illegal immigration was threatening the nation’s safety. In another midterm rout year for Republicans, he gave up a safe Senate seat and won.

By then, Mr. Zeldin was already eyeing his next step up: a run for New York’s highest office. Everything in his experience suggested the timing — the midterms after Democrats swept into power — would make for the ideal conditions.

Even as he has softened some of his positions, like those on abortion, some of Mr. Zeldin’s proposals around crime have already attracted legal and racial scrutiny. He has, for example, pledged to fire the district attorney in Manhattan, the first Black man elected to the office, on his first day as governor. And after criticizing Ms. Hochul for maintaining a state of emergency during the coronavirus pandemic, Mr. Zeldin has said he would declare a crime emergency to allow him to suspend the state’s bail law. Democrats say the pledges are demagogy and argue that Mr. Zeldin has no serious plan on inflation, either.

But in a state where even Republicans have so internalized their own low chances of winning that the party often fails to field top-tier candidates for major offices, the very fact of Mr. Zeldin’s competitiveness has also triggered unfamiliar enthusiasm.

To many of his supporters, including some moderate Democrats, the specific policies are less important than the message that Mr. Zeldin will stop at nothing to fight crime — a message that has at times become unexpectedly personal.

In recent months, Mr. Zeldin became a regular presence at scenes of brutal crimes. Subway slashings. Shootings. Acts of hate against Orthodox Jews and Asians.

Then, in mid-October, one found him. While he was marching in a Columbus Day parade in the Bronx, gunshots erupted near his home, a freakish coincidence that sent his twin daughters into hiding.

Flanked by his family back home that night, Mr. Zeldin did not miss a beat when addressing reporters.

“We cannot surrender any street anywhere in the state of New York to criminals,” he said. “I’m standing in front of crime-scene tape in front of my own house. You can’t get me more outraged than right now.”

Kirsten Noyes contributed research.