Matt Castelli’s Long-Shot Race to Defeat Elise Stefanik

GLENS FALLS, N.Y. — Matt Castelli has spent much of his career in the shadows.

Over nearly 15 years at the Central Intelligence Agency, he hunted down terrorists in one way or another. Half-Sicilian, with a glistening black beard, he has the look of a global Everyman — someone who you might imagine, in the immortal words of Indiana Jones, “speaks a dozen languages, knows every local custom” and can “blend in, disappear” in any society.

Much of what Castelli did in government service he can’t talk about — so it’s hard to know exactly what his accomplishments are. Now, after stints with the National Security Council under the Obama and Trump administrations, Castelli is attempting a radical career shift.

He’s running to unseat Representative Elise Stefanik, the No. 3 Republican in the House, who has made an abrupt transition of her own — a Harvard-educated darling of the G.O.P. establishment who is now a pro-Trump bomb-thrower.

Castelli, 41, has not received much help from national Democrats, who have all but written off Stefanik’s upstate New York district as a lost cause. In 2020, she won re-election by nearly 18 percentage points, running nine points ahead of President Trump.

But after trouncing his primary opponent, a more progressive Democrat, by more than 60 percentage points in Tuesday’s primary, Castelli argues that he has more of a chance to win the North Country, as the area is known, than party officials and pundits expect. (Stefanik ran uncontested.)

“This is a moderate district,” Castelli said last week over beers at Fenimore’s Pub in Glens Falls. “And Stefanik is no longer a moderate.”

A major component of Castelli’s strategy is leaning into that word: moderate. His campaign collected more than 6,600 signatures to put him on the ballot for the Moderate Party, taking advantage of New York election laws that allow candidates to run on multiple tickets. That total was more signatures than he collected to make the Democratic Party ballot and nearly twice as many as the rules required.

He figures there could be thousands of independents and disaffected Republicans who might not stomach voting for a Democrat but would choose a Chevy-pickup-driving, American-flag-waving national security specialist who is not shy about rejecting the left-wing inclinations of, say, Representative Alexandria Ocasio-Cortez of the Bronx.

Motivated after Sept. 11 …

Raised in Poughkeepsie, N.Y., by a Republican mother and Democratic father, Castelli played baseball in high school, then went to Siena College, a private Franciscan institution near Albany. He was inspired to get a master’s degree in national security studies at Georgetown University after Sept. 11, then joined the C.I.A., where, he says, he “straddled” the agency’s operational and analytical wings as a targeting specialist and, later, a leader of various teams.

After spending five months in Barack Obama’s National Security Council, he spent a year as a director for counterterrorism in Donald Trump’s tumultuous National Security Council, serving under Lt. Gen. Michael Flynn, then Gen. H.R. McMaster. Castelli then returned to the C.I.A. for about two years in a liaison role while attending business school at Northwestern University on the side, before leaving for the private sector.

During his time in two administrations, Castelli also had a front-row seat to the rise of groups like the Islamic State, which gave him a direct appreciation for the blowback America faced in the Islamic world after the wars in Afghanistan and Iraq. After seven C.I.A. officers were killed by a suicide bomber in 2009 at an American base in Khost, Afghanistan, Castelli took a more “operational role,” he said, declining to go into details.

… and again after Jan. 6

But it was the Jan. 6, 2021, attack on the Capitol, Castelli says, that motivated him to leave his job at a health care company to run for public office.

Last year, he moved upstate for the first time and now lives in Glens Falls, an old lumber-mill and paper-factory town near Lake George, and announced his run against Stefanik in September. That has fueled the accusation from Stefanik’s local political machine that Castelli is a carpetbagger — a transplant from Washington, D.C., or, worse, Poughkeepsie.

In Castelli’s telling, however, his decision to run against Stefanik was inspired by her defense of Trump and embrace of his conspiracy theories about the 2020 election — even after the assault on the Capitol — offended his sense of patriotism.

“It was an attack against our country,” he said. “For those of us who swore an oath to the Constitution, this was an effort to overturn all of that. And for me, it was galling.”

Castelli estimates he has put at least 40,000 miles on his Chevy driving around the 21st District, which, at around a third of the state, is one of the country’s largest by geographic area. Plattsburgh is the district’s most populous city, but most of the area is rural — and Stefanik was known to run up 40-point margins over her previous Democratic opponents.

It also contains all of Adirondack Park, which includes the blue-tinged summer playgrounds of Lake Placid and Saranac Lake, as well as Cooperstown, home of the Baseball Hall of Fame.

But the sprawling district’s center of gravity, if it has one, is the farmlands of the Mohawk Valley, which is decidedly Trump and Stefanik country.

That daunting political geography, combined with Castelli’s lack of political experience and the fact that Trump won the district by 10 percentage points in 2020, may help explain why so many analysts have discounted his chances.

Like the polished agency briefer he once was, Castelli has a ready response for that, too. He pointed out that not only did Biden close the gap with Trump in 2020 after Hillary Clinton was trounced there in 2016, but Obama won the district by six percentage points over Mitt Romney in 2012, just as he beat John McCain there in 2008.

“At the end of the day, there’s still a sense of independent-minded folks here,” he said. “There’s a sizable contingent who are concerned with the extremist wing of the Republican Party that Stefanik is leading.”

That’s highly debatable: The North Country, with a median household income in the $40,000s, is the kind of place where Poughkeepsie might as well be Park Slope, and the skinny jeans and tucked-in shirts that Castelli wore early on are signifiers of an urban sensibility.

Reading the district

Before Stefanik first won her seat in 2014, an earlier version of the 21st District was held by Bill Owens, a moderate Democrat. And portions of the area were previously within Kirsten Gillibrand’s House district, before she became a senator.

Stefanik isn’t likely to be caught napping. A political animal known to pore over her own media clips, she has held more than 2,000 events in the district since taking office. Her name recognition easily dwarfs that of Castelli, a relative unknown. She has transferred $3 million from her own campaign coffers to assist other Republicans — a sign of her supreme confidence that she will fend off yet another Democratic challenger.

As for Castelli’s critique that Stefanik has not paid due respect to the law-enforcement officers injured on Jan. 6, or that her attacks on the F.B.I. for searching Mar-a-Lago will backfire, there’s no concrete sign of that. Her team is confident that voters in the district will care far more about the prices of gas and groceries — an issue on which Stefanik has been extremely vocal.

“If he wants to run as a Joe Biden Democrat, good luck,” Stefanik said in a brief telephone interview. “The only Joe Biden signs you see in this district have expletives with them.”

For now, Castelli is trying to change the narrative that he has no hope of dethroning one of the Republican Party’s rising stars. He has compared notes with former Representative Antonio Delgado, a moderate Democrat who flipped New York’s nearby 19th District before being tapped as lieutenant governor by Gov. Kathy Hochul in May. Delgado, he said, won the seat in part by outworking his opponent, a strategy he has taken to heart.

To the surprise of some analysts, a special election for Delgado’s former seat was won on Tuesday by a Democrat, Pat Ryan — which Castelli cited as another “proof point” that Stefanik is beatable.

“It’s about showing up,” he said. “It’s about affording the voters the opportunities to be heard, regardless of party.”

Stefanik said she would give no quarter.

“When I ran, I did 100,000 miles,” she said, referring to her 2014 race. “The media always underestimates me, and we always overperform on Election Day. I will not be outworked.”

What to read

• Since the fall of Roe v. Wade, it’s increasingly hard to see the once-clear signs of a G.O.P. advantage, Nate Cohn writes in The Upshot.

• A series of strong special election showings, culminating in a New York win, have buoyed Democratic confidence, but a daunting map may still cost them the House.

• President Biden announced a plan to cancel student loan debt and extended a pause on payments for all borrowers. The debt relief is likely to face legal challenges.

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