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Read it in the Greenwich Sentinal

Fool Me Once, Shame on Me. Fool Me Twice…

By Mike Hahn

A response to Jill Oberlander’s “independent” mailers — from the people who have read this script before.

Jill Oberlander wants you to know she’s a middle child and a redhead, and therefore “a little feisty.” She promises that “some days, I’ll vote with my party. Other days, I won’t.”

Stop. Greenwich has heard this speech before. Word for word.

Steve Meskers gave it. Hector Arzeno gave it. Every two years, our Democratic state representatives swear they are independents first; that they’ll stand up to Hartford and defend local control. And every session, when the Democratic machine actually needs their vote, the “independence” evaporates on schedule. Don’t take our word for it. Take the roll call.

Fool Me Once: The Meskers-Arzeno Playbook

In 2024, after years of promising Greenwich they would defend local zoning, Meskers and Arzeno both voted for HB 5390; “Work, Live, Ride,” Desegregate CT’s own transit-oriented development bill, written to leverage away local authority over development around our train stations. When the Democrat bosses pressured them, they buckled.

In 2025 they perfected the act. HB 5002 was rewritten on the House floor, by a Democratic strike-all amendment, into a sweeping “fair share” housing mandate aimed straight at towns like Greenwich. Arzeno and Meskers voted for the strike-all amendment that built the bill. They voted against every Republican amendment that would have actually protected Greenwich’s zoning, the amendments Ryan Fazio and Tina Courpas fought for. And only then, with passage already secured, did they cast a carefully timed “no.” The bill passed 84-67 anyway. Only Governor Lamont’s veto saved Greenwich. That is not independence. That is a permission slip, stamped in advance by leadership for the district that needed cover.

The pattern runs beyond housing. The 2025 Trust Act expansion, inviting lawsuits and legal fees against our own town and police, passed near party-line: Arzeno yes, Meskers yes. The $55.8 billion budget that gutted the fiscal guardrails, draining roughly $600 million a year from the volatility cap and parking spending in off-budget accounts, Arzeno yes, Meskers yes, and no on every Republican alternative. Some days with the party, some days not? Find the days.

Fool Me Twice: Oberlander Already Auditioned

Oberlander has already had her moment to show Greenwich what her “independence” looks like. It’s in the Board of Selectmen record, March 11, 2021.

That morning, SB 1024, the DesegregateCT bill written to strip Greenwich’s Planning & Zoning Commission of authority over development near our train stations and along the Post Road, was moving in Hartford. First Selectman Fred Camillo asked his Board for one thing: a unified statement defending local control. Lauren Rabin said yes on the spot.

Oberlander’s answer, from the transcript: “I wish you had given us a little bit of heads up.” Then: “I’m not sure where I stand on any of these proposals.” And: “I’m not comfortable giving a blanket approval of a statement on behalf of the Board of Selectmen.” Camillo had to go around his own board and issue a statement alone. With Greenwich’s zoning authority on the chopping block, she could not bring herself to say no to Hartford.

Her BET record tells the same story. She chaired that board during its most partisan modern stretch, and in her entire tenure there is not one documented instance of her breaking with the Democratic caucus on a contested vote. Not one.

And the 2026 version? She told Lisa Wexler’s audience she’s “definitely not in the progressive end of the party”, then hired her campaign manager through “Jobs That Are Left,” a job board that exists solely to staff progressive campaigns. She says she supports the fiscal guardrails, then hedges that “a little give and take” may be needed, which is exactly how guardrails die in Hartford. She calls herself a “strong supporter of local zoning”, and backed the special-session housing bill.

The “Seat at the Table” Con

Her closing argument is that Greenwich needs a senator “with the majority.” Hartford Democrats hold 25 of 36 Senate seats and 102 of 151 House seats, a veto-proof supermajority that can pass anything without a single vote from this district. That majority doesn’t negotiate with freshmen. It needs her for exactly one thing: to be vote number 26.

Fool me once, that was Meskers and Arzeno, promising independence and delivering permission slips. Fool me twice? Oberlander is betting, 82 days out, that Greenwich, North Stamford, and New Canaan won’t recognize the third performance of the same play.

She’s already told us what she does when her town needs her: “I’m not sure where I stand.”

We are.