JUDGE ST. — After more than a decade in the armed forces and two years as President Joe Biden’s Director of Counterterrorism, Cait Conley packed her bags for NY-17, declared her campaign to defeat Mike Lawler, and immediately became one of the Democratic Congressional Committee’s favorite horses.
The West Point graduate and special operations combat veteran is trying to win one of the most competitive congressional races in the country with a patriotic strain of local pride—invoking phrases like “where I come from,” despite never previously living in the district for which she is running.
When she announced her bid in 2025, Conley said she moved to the Hudson River town of Ossining and included it in her campaign launch video, which she filmed in Virginia.
In an email to supporters two weeks ago, Conley’s campaign misspelled her current residence of “Ossinging” as well as two other neighboring towns—”Chapaqua” (two Ps) and “Poundridge” (two words), Politico reported.
“If you’re trying to beat the carpetbagger label, step one is spelling your ‘hometown’ correctly,” Lawler’s campaign manager taunted.
But as it turns out, Ossining is not really her place of residence. According to a review of property records and voter information by the Judge Street Journal, Conley’s home is technically part of the Town of New Castle—a neighboring municipality that includes the hamlets of Chappaqua and Millwood. In November, Conley voted in Chappaqua, not Ossining.
The Journal will not publish her address, but residents who grew up in the district refer to her neighborhood as Millwood—and most know it best because of Rocky’s, the iconic deli open 24/7.
“It’s Millwood,” a Rocky’s employee told the Journal when asked the name of the area.
In response to an inquiry for this story, Conley’s team sent the Journal a written statement from one of her allies.
“As the former Ossining Town Supervisor, current chair of the Ossining Dems, and a former Westchester County Legislator representing Ossining, I believe it is not wrong for Cait to say she lives in Ossining,” Catherine Borgia wrote. “Her address is Ossining, she is in the Ossining school district, she is a member of the Ossining community.”
Conley’s home is on the very edge of Ossining’s school district—her neighbors across the street belong to Chappaqua’s—and she’s eligible to vote in several local New Castle elections.
Given the choice between the multiracial working-class community of Ossining and the upscale enclave of Chappaqua—where the Cuomos and Clintons have put down roots, and SAT prep begins before 9th grade—it makes sense that Conley declared the former as her home base in the battle to reclaim NY-17.
In October, amid a field of eight contenders in NY-17, the DCCC picked Conley and one other competitor to attend its “Candidate Week” in Washington. Two weeks ago, rising Democratic powerhouse Congressman Pat Ryan, who represents the neighboring NY-18, endorsed her in an exclusive statement to the Journal.
The revelations about her residence are the latest in a series that has demonstrated her artificial familiarity with the district. Conley’s opponents have an opening to hit her as a carpetbagger who was fighting in another country while they were working as part of the local community—if they can thread that needle without dissing her service record.
To hear Conley tell it, she’s a public servant, not a politician, which is why people should vote for her. But the 40-year-old upstart may find the limits to that argument in one of her opponents, former Briarcliff Mayor Peter Chatzky, who spent the last two decades ingratiating himself in Westchester politics.
The 64-year-old retired tech tycoon recently dumped $5 million dollars into his war chest, and he’s running a campaign that is effectively the opposite of Conley’s in both style and substance: soft-spoken, affable, built on old community ties, and comfortable with a wide range of progressive politics, from abolishing ICE to investigating Israel’s war crimes in Gaza.
The DCCC has struggled to figure out how to win in NY-17, and it’s hoping that Conley’s centrist politics will appeal to purple voters. Last cycle, former Congressman Mondaire Jones moved back to the district after a failed primary bid in lower Manhattan, but despite his efforts to tack to the center, he lost handily.
Just one district south, in NY-16, Westchester County Executive George Latimer—an unassuming rockstar with local wine moms and a 30-year fixture in local politics—unseated Squad member Jamaal Bowman in a vicious primary that torched the congressman’s lefty bonafides.
The political class wondered if progressive politics had become a liability for suburban voters—Jones lost because of his old Defund the Police statements, and Latimer won because of his “commonsense” politics. But there is another thread that binds Jones’ defeat with Latimer’s victory: the lengths of their residency in the district.
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Great piece. One additional point for your conclusion--Latimer won also because his common sense wasn't troubled by receiving more than $19 million in support from the Israel lobby. Also, thanks for updating us re Conley and her connections to Palantir, Hidden Level and Primer AI!