By Gretchen Webster
WESTPORT–Questions ranging from problems with downtown parking, to affordable housing, to the future of the Cribari Bridge in Saugatuck were some of the hundreds of questions provided by Westport Journal readers for the Journal’s First Selectman Candidate Debate Thursday held at Greens Farms Academy.
Not all of the questions could be answered at the debate. The three first selectman candidates responded to questions chosen by Moderator Jeff Wieser, some directed at perceived weaknesses in the candidate’s background or behavior, and others confirming their most important goals.
Biggest issue?
Wieser, who is also the moderator of the Westport Representative Town Meeting, first asked the three candidates: Democrat Kevin Christie; Don O’ Day, who is endorsed by the Republicans; and David Rosenwaks, representing the Independent Party, what they see as the biggest issue facing Westport.
Christie called the need to upgrade and repair the town’s infrastructure including town buildings, the biggest issue facing the town. O’Day’s top issue was the length of time it takes to get projects done in Westport. Town officials need “to find consensus to allow projects to move forward, “he said.
Rosenwaks named “transparency,” as the biggest issue he thought Westport is facing. He pledged “better communication and accountability.”
Criticisms
One set of questions posed by Wieser were directed at criticisms made against each candidate in the past. O’Day was asked about his connection to the national Republican Party, Rosenwaks about a perceived lack of leadership experience, and Christie about recusing himself from a vote on renewing the contract of soccer coach Russell Oost-Lievense, as a member of the Board of Education.
Christie said he recused himself because of connections he and his family had with the Staples and Westport soccer programs. Being a CEO is different from being a board member; he said he would be “more than comfortable” making hiring and retention decisions as First Selectman.
O’Day said he is “somebody who can work in a nonpartisan way … I have no relationship to the national Republican Party,” he said. And Rosenwaks cited his history in financial management, managing millions of dollars, and hundreds of personnel.
Parking deck
All three candidates spoke in favor of building a parking deck in the Baldwin Parking lot to ease parking problems downtown. “The difference between me and [First Selectwoman] Jen Tooker is I’m open minded about a parking garage,” O’Day said. Christie and Rosenwaks agreed that the two-hour parking limits now in effect in downtown Westport are too short, and that the downtown merchants should be included in making future parking plans. “Merchants need to have a seat at the table,” Christie said.
Community gardens
When asked about the future location of the Community Gardens, Christie said he was “committed to rebuilding the Community Gardens,” and saw the Burr Farms field as providing the sunlight, topography and parking that the gardens need. O’Day said that if there were a proposal to place the gardens at Burr Farms “Little League would have to give up a field,” and that he trusted Parks and Recreation director Erik Barbieri to review the locations and make the best decision.
Rosenwaks agreed with Christie that Burr Farms would be a good location to rebuild the Community Gardens. “The gardeners have not been treated right,” he said.
Cribari bridge
The fate of the historical Cribari Bridge in Saugatuck, was a concern to all three candidates who wanted to preserve its character, and wanted to keep large trucks from crossing the bridge into Saugatuck, in whatever way they could. But O’Day said the town should not own the bridge because of the cost of maintaining it – in the millions. “It would be fiscally irresponsible for the town to own the bridge,” O’Day said.
Different from today?
For the last question, Wieser asked the candidates “what is the one thing you would do differently from the current administration?” Christie said he wanted to make the town more community centered, and O’Day said he wanted to see the Selectman’s office meeting with the Planning and Zoning Commission for a “pre-app” meeting to make the 8-24 process of redesignating the use of town-owned land shorter and more understandable. And Rosenwaks said as first selectman, he would need to see more projects completed – and faster. “I want action – I see a lot of inaction.” he said.
To view a video recording of the debate, please click here.
A correction was made on Oct. 18, 2025: An earlier version of this article mischaracterized Kevin Christie’s vote as a member of the Board of Education. Christie was not part of the vote to uphold the superintendent’s decision to not renew a coach’s contract.
As the lead sponsor of the RTM’s ordinance on gas leaf blowers, I feel the need to correct a mis-statement by Mr. O’Day at last night’s debate. He said he’d voted for the summertime restrictions on use of gas blowers, when in fact he was one of 9 RTM members who voted against it. I would also like to note that at the Sustainable Westport debate, Mr. Rosenwaks said he had voted against the lease of more than $800,000 in gas-powered equipment for golf-course maintenance, when in fact he voted for it. RTM members’ voting records are available here: https://www.westportct.gov/government/elected-officials/representative-town-meeting-rtm/voting-record-attendance.
Ms. Schneeman, You seem more interested in splitting hairs about what two of the candidates said or how they voted than attending an important meeting at the library about turning Jesup Green into a parking lot which is right in the middle of the district you represent.
So when the LLSBC said that Westporters wouldn’t expect them to remove a facility without a plan to replace it, they were lying?
Don O’Day seems to be the candidate of the sports daddies.
I’d like to express my sincere appreciation to the Westport Journal for its balanced, thoughtful, and truly nonpartisan coverage of the recent First Selectman Candidate Debate. Your reporting continues to reflect a genuine commitment to community journalism — asking the hard questions, giving all perspectives a fair voice, and focusing on the issues that matter most to Westport residents.
It’s refreshing to see a local publication maintain such integrity and depth in its reporting, especially during election season. Thank you to Gretchen Webster and the entire Westport Journal team for providing clear, factual, and even-handed coverage that helps our community stay informed and engaged.
As Kristin Schneeman points out, facts matter.
And because some candidates can (and will) say almost anything to prop themselves up and camouflage their disqualifying shortcomings that would lose them votes, it is critically important to thoroughly “vette” candidates and their assertions. Unfortunately most voters just “trust” what they are told, and few have the time or desire to do that vetting.
So here are TWO critical misrepresentations that Mr. Rosenwaks has repeated at every chance he gets including at last evenings debate:
1. Claim: “I started my own asset management company”. Mr. Rosenwaks is referencing StoneCastle Partners, LLC.
The Truth: StoneCastle Partners: “MR. JOSHUA SIEGEL founded StoneCastle Partners LLC in 2003, and serves as managing partner, chairman, and chief executive officer. He is widely regarded as a leading expert and investor in the banking industry.” http://www.scpdevco.com/people/josh-siegel
The Truth: Mr. Joshua Siegel (CEO and Chairman) and Mr. Matthew Mayers (General Counsel and Chief Compliance Officer) were the only two “Executive Officers” of StoneCastle Partners, while Mr. Rosenwaks was merely a “beneficial owner”.
https://www.sec.gov/Archives/edgar/vprr/0505/05053108.pdf
The Truth: Mr. Rosenwaks has never had any business school education, never had any SEC certifications, had no SEC registrations, and has had zero fiscal responsibilities in nearly two decades. It was only Mr. Joshua Siegel who was SEC registered and held multiple investment certifications.
https://files.brokercheck.finra.org/individual/individual_3131719.pdf
2. Claim: “I am running as an independent that way I will not have to answer to anyone.”
The Truth: The ONLY reason Mr. Rosenwaks is running as an independent is because he failed to receive the DTC’s endorsement. There were good reasons for that denial.
The Truth: When someone is endorsed by the Independent Party they must take an Oath and “Sign the Pledge Statements” and email to info@ctindependents.org. The pledge statement mandates
“I will actively co-sponsor and support legislation advancing the responses I have given to the questions asked by the Independent Party of Connecticut in selecting candidate endorsement.”
The Truth: There are currently FIFTEEN current bills in Hartford that the Independent Party candidates are pledged to support or oppose, including:
Independent Party of Connecticut actively OPPOSES HB6263 “AN ACT CONCERNING THE USE OF AND PURCHASE OF GAS-POWERED HAND-HELD OR BACKPACK GAS POWERED LEAF BLOWERS BY STATE AGENCIES”
This bill’s purpose is to eventually prohibit the use of hand-held or backpack gas-powered leaf blowers in the State.
Independent Party ACTIVELY SUPPORTS HB6831 “AN ACT SUPPORTING TRANSIT ORIENTED COMMUNITIES” and SB1252 AN ACT ESTABLISHING PRIORITY HOUSING DEVELOPMENT ZONES
As famously said, “You can fool some of the people some of the time…”, and given Mr. Rosenwaks’ self-professed lifelong ambition to “be a performer”, his campaigns continuous barrage of rhetoric, ambiguity and spin, combined with his aversion to providing facts and specifics, along with his newness to Westport and lack of meaningful local track record (apart from his unremarkable 2 year RTM tenure), fact checking his assertions becomes even more critical because deceiving the public has serious consequences.
Performance art IS NOT what Westport’s residents are looking for in our First Selectman.
Transparency cannot just be a campaign thesis: it has to be evident in the behavior of anyone involved in town governance, including candidates.
The first time I raised a transparency issue in Westport was at the First Selectpeople’s Board meeting in the Summer of ‘23. I went to the meeting to get information I had sought unsuccessfully for a month or more: Was the Community Garden at risk in the context of a new school? At this point it was just a rumor,
Moore (now seeking reelection) tried to muzzle me and others in attendance by cutting us short or by trying to block us from speaking at all, on a false procedural.
Then Jimmy Izzo gingerly stepped to the podium up champion the current boss lady and declare unequivocally what a wonderfully transparent government we had; he’s used this refrain frequently since then.
And I never got an answer.
O’Day is anti-transparent and has worked hard on several occasions to keep the public out of the loop; he thinks he knows what’s best for us.
Every candidate who speaks of transparency and open government can stake their claim only through their own honesty and actions.