ICYMI: Carpetbaggin’ Cait’s No Good, Very Bad Week

Hello,

Since her campaign launchcarpetbaggin’ Cait Conley has claimed to live in Ossining, NY, but a bombshell report reveals she actually resides in the ritzy town of New Castle.     And this comes just days after Conley’s own campaign misspelled Ossining, as well as the towns of Chappaqua and Pound Ridge, in a press release.

Read the full story here or see excerpts below:

Conley’s Congressional campaign touts her residence in diverse Ossining, but she actually lives in elite New Castle
Hudson Valley Digger
David McKay Wilson
January 23, 2026

  Here’s a tip for newcomers to Westchester: your address is not necessarily where you live. It’s a tip that Cait Conley, the national security official in the Biden administration who moved to Westchester in 2025 to run for Congress, may need to review.

[…]


In her launch video, Conley identifies herself as “Democrat for NY, Ossining NY” in its opening frames as she’s pictured doing pull-ups in the gym and parachuting in combat garb during her stint in the US Army.

Supporters say her campaign headquarters are at her home, with Ossining listed as her campaign’s location on her Linked In page. The Conley campaign’s mailing address is an Ossining post office box.

Conley’s campaign is all in on Ossining. But a Hudson Valley Digger investigation found she does not live in the diverse Hudson River town.

While the home’s mailing address is in Ossining, her home is located New Castle’s Millwood neighborhood on the western edge of the town, according to New Castle assessment records. New Castle, one of Westchester’s toniest suburbs, is the hometown of Bill and Hillary Clinton, and was the home of Andrew Cuomo during his tenure as New York governor.

[…]

Maureen O’Toole, a spokeswoman for the National Republican Congressional Committee, said that the Conley’s declaration that she lives in Ossining casts doubts on her campaign.

“Carpetbagging Cait Conley can’t even be honest with Hudson Valley voters about where she lives,” O’Toole said. “They sure as hell can’t, and won’t, trust her to represent them in Congress.”

[…]

Maureen O’Toole
Eastern Regional Press Secretary
motoole@nrcc.org | @MaureenOToole4

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