An informed electorate is the greatest bulwark of democracy.
Westporters understand this is a very important election. “06880” is doing our part, to help Westporters understand candidates’ perspectives on a variety of issues.
Once a week, between now and Election Day, we’ll ask the men and women running for 3 important boards — Selectmen/women, Planning & Zoning, and Education — one specific question.
We’ll print their responses verbatim.
This week’s question for the Board of Selectmen/women is:
Every candidate brings their own style to Town Hall. How would your administration differ from the current one? And how would it be similar?”
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Republican Party-endorsed candidates Don O’Day and Andrea Moore say:
Every 1st selectman brings their own style and priorities to Town Hall. While I respect the work and tireless dedication of the current administration, I will bring my own approach to the job.
My style of leadership, as demonstrated during my time as chair of the Board of Education and as chair of the successful renovation of Coleytown Middle School, emphasizes clear communication, strong collaboration, fiscal discipline, and a hands-on management approach.
I share many of the same goals as the current administration. where my running mate Andrea Moore serves as 2nd selectwoman. Those shared goals are keeping Westport safe, welcoming, well-managed, financially strong, all while maintaining our reputation as one of the most desirable towns in the country to live and work.
Don O’Day and Andrea Moore.
How We Will Differ?
Our first priority will be improving how the town communicates with residents. Too often, people learn about major projects once progress has already been made.
We can do better. We will use technology, including short video updates, to explain what is happening, why it matters, and what comes next. The way I handled Coleytown Middle School updates is a great model: clear, consistent and transparent. It is the standard we will set for every department.
We will also strengthen collaboration between the 1st selectman’s office and the Planning & Zoning Commission. Using a renewed focus on the pre-application process before any 8-24 review; we will align projects early, reduce friction, and eliminate surprises. Early communication makes for better projects and a smoother process.
Each department will have clear and measurable goals that we will evaluate on a regular basis, including those related to sustainability and affordable housing levels. We will publish results, celebrate success, and be honest about setbacks.
When mistakes happen, we will acknowledge them, fix them, and move on. That is how trust is built.
We will take a more visible role in presentations to the Board of Finance and RTM. Residents will see their leaders working together, openly, toward shared goals.
We will be respectful listeners, but also clear and factual communicators. A small but vocal group advocating for a certain result can sometimes drown out the views of less engaged residents. We will address misinformation directly and calmly, ensuring that all residents have the facts they need to make informed decisions.
In short, our administration would focus on openness, clarity, and collaboration to rebuild confidence in how our town gets things done.
How We Will Be Similar?
Like the current administration, I understand that the 1st selectman’s role is, above all, a management job. The safety of our residents, the reliability of town services, and the day-to-day operation of departments come first. Westport has outstanding professionals serving our community, and I share the current administration’s appreciation for their dedication and expertise.
We also share a commitment to keeping Westport economically strong, and this is an area of significant strength for Jen Tooker, who supported the establishment of the successful Startup Westport.
We all know that a healthy business community keeps our tax base stable and helps maintain the high quality of life we all value. We will continue efforts to attract new businesses and support those already here, helping them thrive while preserving the character of our downtown and neighborhoods.
Like the current administration, we will work tirelessly every day to manage what makes Westport special: strong schools, the arts, open space, and civic engagement. Those priorities are not partisan; they are Westport.
In Summary
An O’Day/Moore administration will build on what is working today while improving how we communicate and collaborate. We will get things done.
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Democratic Party-endorsed candidates Kevin Christie and Amy Wistreich say:
Let’s start with the similarities: We all love Westport.
However, our leadership will be extraordinarily different from the current administration (which includes our Republican opponents, with a core member of the Long Lots School Building Committee and the current 2nd selectwoman), and our Independent Party opponent. We:
Will be hands-on leaders who show up. On Day 1 of construction for Westport’s most significant capital project in history, no senior town officials were there, and as a result, a neighbor’s ~6,000 square feet of protected plantings were destroyed. We will work hand-in-hand with the Building Committee, Board of Education and the state to ensure that Long Lots/Stepping Stones is on time and on budget, engage all stakeholders, and ensure that construction is managed with the appropriate oversight.
Kevin Christie and Amy Wistreich.
Will fund by vision. Under the current administration, the town’s capital plan has expanded to a $500 million laundry list of proposed projects over the next decade. We will proactively prioritize capital projects and initiate a comprehensive review of the 10-year capital plan with the Board of Finance, RTM, Board of Education, and the public to enhance transparency and trust as we plan and fund key projects.
Will bring vision and urgency to Saugatuck. Our plan will include appropriately scaled mixed-use development near the train station and I-95, and other development that serves local needs, reflects Saugatuck’s history and identity, protects its fragile waterfront, and keeps it publicly accessible.
Care about housing diversity. We have the tools already (the Affordable Housing Trust Fund and Committee, potential partners like the Housing Authority and Homes with Hope) to build the affordable housing we need while protecting open space. We’ll bring those partners together and turn plans into action to serve more workers, seniors, and young people.
Will mitigate flooding. We must, and will, make flood resiliency a town-wide priority. We will develop forward-looking plans to prevent damage to our homes and property from coastal and inland flooding, partner with local and state experts to map risks and develop flood mitigation plans, revise our clear-cutting guidelines, evaluate critical infrastructure in flood zones, and educate homeowners about maintenance, buffers, and storm readiness.
Are fed up with dead-end studies. At the top of the list is downtown. The Downtown Plan Implementation Committee was formed 10 years ago. What has been implemented? Westport residents, businesses, and visitors deserve better than the parking lot that occupies precious waterfront property. We deserve better than confusing and constantly changing parking regulations. We will execute a cohesive downtown parking and Parker Harding Plaza improvement plan and get it done. Now is the time for effective stakeholder engagement and decisive action.
Will not ignore national issues that hit locally. We won’t stay silent on racism, book banning, antisemitism, funding cuts, or ICE presence in our community. As Democrats, we will be the firewall against this agenda.
Will work for the environment. For example, we will preserve Jesup Green and protect Longshore’s natural beauty, including its trees and not spending nearly $1 million on gas-powered machines, taking a different approach from our Independent Party opponent.
Westport deserves leaders who actively work to solve problems. We are the right team with the right experience, in finance, strategy, real-world planning and problem solving, and leading complex transactions.
We won’t back away from hard problems or conversations. We will bring fresh energy to the job, and we look forward to earning your vote and getting to work on your behalf.
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Independent Party-endorsed candidate David Rosenwaks says:
My goal is to continue balancing fiscal responsibility with the high quality of life our residents expect.
How will I lead differently?
Integrity first. Service over self: more servant leadership, less personal positioning. Fairness and impartiality must be visible priorities. My goal: honest, transparent communication. Even when it’s hard; that will be the standard I hold for myself and my team.
Stronger community engagement—with faster results. Downtown parking, traffic and infrastructure improvements have dragged on for years. Residents and business owners alike are frustrated by the lack of meaningful progress. My goal: make these issues top priorities with open communication, clear timelines, and visible results so people see alignment between process and outcomes.
David Rosenwaks
Stronger partnerships with the Connecticut Department of Transportation and developers. CTDOT controls major roads like the Post Road and Route 33. Local improvements — crosswalks, signals, safety measures — depend on a strong working relationship with the state. The Cribari Bridge project will shape our downtown for decades; I’ll ensure Westport’s vision guides the state’s actions. Likewise, I’ll bring constructive engagement to builders and developers. The Saugatuck development litigation shows what happens when communication breaks down. My goal: leadership that listens, collaborates, and influences outcomes that serve the town’s best interests.
Annual, transparent long-term strategic planning. In June 2025, the town approved the largest appropriation in Westport’s history: over $100 million for a new Long Lots Elementary School. Our AAA bond rating is a strength, but total bonded debt will rise considerably, and while we are still well below our 7x tax-to-debt limit, the financial environment is changing rapidly. We can’t manage year to year — we need a forward-looking plan that anticipates challenges in infrastructure, sustainability and demographics. My goal: lead an annual long-term strategic plan that connects fiscal discipline to the future we want for Westport.
Environmental stewardship and resiliency. From flooding and coastal resilience to energy efficiency in public buildings, environmental stewardship must be built into every plan — not added after the fact. It’s not just good policy; it’s sound fiscal management. The lack of proactive environmental oversight in our schools has contributed to the challenges we face today. My goal: bring environmental stewardship to the forefront and integrate it into every major decision.
Modernization and technology in government. Town systems and communication channels are outdated. We can modernize by improving transparency, accessibility, and service through better technology—from digital permitting to real-time updates. My goal: offer residents the most efficient, responsive government possible, including a simple dashboard to track issues, progress, and results.
A higher standard for civic culture and unity. There’s been division and fatigue in our community. That fatigue isn’t from one event — it has accumulated over time because of slow progress, miscommunication, polarized issues, and high stakes for taxes and development. Many residents care deeply, but repeated missteps have led to frustration, disengagement, and significant division. Leadership should unite, not divide. The very nature of my independent status means I work for Westport, not my political party. My goal: restore trust, foster shared values, and renew civic energy. I want to invite more voices into decision-making and ensure every resident feels heard and respected, regardless of party, position or influence.
Westport deserves leadership that acts with integrity, delivers results, and inspires confidence. That’s the leadership I offer.
Your voice. Your town. Your government.
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For last week’s “Where we Stand” question, click here.
For our first “Where We Stand” question, click here.
Kevin Christie and Amy Wistreich nail it. They’ve been paying attention and have the right vision and roadmap to fix the leadership void in Westport under the GOP candidates for far too long.
They are not afraid to stand up to national issues that have immense consequence on our freedoms and way of life locally.
Kevin and Amy’s track records are beyond reproach. They bring proven leadership, financial acumen, land use expertise and shared values that put Westport residents first among competing interests.
Let’s get this done, Westport. Vote for change now. Vote for Kevin and Amy.
Kevin “recuse myself” Christie not afraid to stand up? We must be talking about a different person…. This is a cute platform for people to make promises about what they will do without having any plans on how to do it. At least it’s in writing so we can hold them accountable.
David is NOT afraid to stand up to national issues that have immense consequence on our freedoms and life locally!
David listens to all and finds a balanced approach.
Let’s get this done westport! People and town over party and politics! Let’s stop the divisive tones people have on blogs too right NOW!
It shocks and dismays me that any Republican can run for any elected office in Westport without first publicly and vociferously distancing themselves from our Democracy destroying President.
Dan I completely agree with you! How anyone can be associated with the ‘Trumpian cult’ or vote for their endorsed candidates is beyond me. If you connect yourself to this so-called political party, you take-on the equities and associations of the party. You are implicitly (if not explicitly) agreeing with the actions, behaviors, decisions, policies, beliefs, traits and values of the “club” you’ve joined. O’Day is gaslighting us when he says these national Republican political issues have nothing to do with our local elections and candidates. Nonsense! “Republican endorsed” is just another way of them saying ‘we own you, welcome to our cult and Project 2025.’
Perhaps the storm broke your internet connection, but when it comes back you might want to check out “Hitler” in Israel today.
This is a great feature, Dan. A few brief thoughts on flooding and the environment. It’s mostly too late to do much about flood mitigation. It was too late in the late 1950s. We’ve overbuilt, and in the process have destroyed sensitive natural water absorbers (we literally paved over wetlands (Baldwin Parking Lot) and we continue to encroach on waterway protection lines everywhere. At this point, in terms of flood protection, it’s essentially every man for himself. And I say that as someone who lives in a FEMA A rated flash flood zone with his exterior utilities heavily chained to the house to keep them from being swept away. I wish things could be different but this is what it is.
As for the environment, I would love to read that someone running for First Selectman would require the town to abide by the gas powered leaf blower ban. Exempting itself from same was not leadership, to state the obvious.
Another spot-on response from David Rosenwaks. Are you unhappy with how decisions have been made in Westport in recent years, whether it be the Hamlet, Long Lots building, the community gardens, downtown parking etc etc? Then don’t elect the people who have been responsible for those decisions into even higher offices. David is the only truly independent candidate, meaning he works for WESTPORT not for his party agenda. And that is who this town deserves. Note – I have yet to see Kevin or Don knocking on my door and explaining their positions, yet I’ve run in to David no less than a dozen times, walking the streets of our town learning what the issues are from our residents. That’s the sign of a people’s politician.
I’m confused how someone will “mitigate flooding” and “work for the environment” when they supported the removal of the Community Gardens and Preserve for a ball field.
I certainly also agree with Dan Katz’s statement. We have a disaster of a Republican administration in Washington, attacking the press, using the tools of government to enforce personal vendettas, attacking academic freedom, etc., put, apparently, Mr O’Day saw this and thought, “those are my people!”
The Democrat candidates “will not ignore national issues that hit locally.”
Sorry, this is a major turn-off!
I do not want national politics in town. I do not want ideological battles in Town Hall.
Just efficient and effective administration of the town’s services (schools, Longshore, etc), laser focus on how taxpayer dollars are used, and a very responsible approach to development that doesn’t make Westport the next Stamford.
That’s the beauty of having David Rosenwaks in the race – independent and level-minded.
With all due respect, anyone who has lived here long enough knows these issues have been in our town and we cannot pretend they aren’t. Westport has faced book banning requests, the threat of ICE raids in towns with whom we share a border (I run many errands in Norwalk as do many Westporters and ICE presence at places Westporters frequent has been well-documented), acts of anti-semitism right in Westport front yards, and we are not immune to the effect of funding cuts thanks to our national landscape. It sounds as if your implication is that you support David Rosenwaks because he *won’t* address these issues and you prefer it that way. Perhaps Dan should pose this in an upcoming question to the candidates, so David can explain why exactly he will *not* address these issues as First Selectman. I’d like to understand that because to me, to say that you refuse to address national issues here is to say you don’t want to address issues that affect Westporters.
No one – and certainly not David – condones anti-semitism and racism. If there are episodes that are specific to our town, I am 100% sure he will address, as he should.
But that’s not national politics. Democrats and Republicans have strong ideological views on these topics. I just hope the town doesn’t get enmeshed in these ideological debates and just focus on solving problems that are specific to our town.
Gianni, I’m not sure how long you’ve been here in town but national issues have impacted Westport several times over the last 8-10 years. We don’t live in a bubble therefore we are not immune to such issues. And you started your comment by quoting Kevin Christie’s, “The Democrat candidates “will not ignore national issues that hit locally.” That clearly says “issues that hit locally” and not “debate” and Christie went on to list examples that have had actual impact here in town over the last 8-10 years. You proceeded to comment that you appreciate that David won’t engage in national politics. I remain confused by that unless you, like David, just haven’t lived here long enough to realize the impact from the national landscape that we have experienced right here in Westport (if that is the case, then I understand and mean no disrespect). Given David’s lack of experience and longevity in town, he might not even be aware of the issues that have occured here – though that certainly concerns me further.
Someone is mischaracterizing David. He most certainly will defend against divisive national politics that hurt people from antisemitism,to racism, to book banning, to protecting people who work in our town.
Sadly, but to be expected, the O’Day/Moore ticket does not distance itself from the present Tooker/Moore ticket. Does that mean they will not do a good job for Westport? No. only that they are unwilling to tell the truth. Ultimately, achievements are almost all that matters. We have rarely had a First Selectperson who addresses and completes the work on difficult issues. The voters deserve to know what each candidate will seek to actually accomplish. The issues and possible solutions are well known to all. I sent each candidate a letter requesting what they would do as to some 14 items that I believe are important, e.g. Baron’s South, allocation of funds between the Town and the Schools, the Community Gardens, a new fire station, The Hamlet, a new Coleytown Elementary School, the leaf blower ordinance, use of Town land for 8-30g housing, whether or not downtown has adequate parking and many more. I received no response from any candidate to my letter.
Lisa Newman spot on. David Rosenwaks has had ample time to participate in our democracy and engage, especially with the Long Lots Elementary project.
We had over 60 plus meetings, all open, all transparent, all involving Westport residents, NOT POLITICS.
Mr. Rosenwaks choose to spend his RTM time in the walk-in cooler when the kitchen of democracy, and local debate got hot.
To claim he is an independent borderlines on laughable.
As of 4 months ago Mr. Rosenwaks was an “ACTIVE” member of the Westport Democratic Town Committee.
This time last year Mr. Rosenwaks was Campaign Manager for State Representative (D) Jonathan Steinberg’s Re-Election Campaign.
David Rosenwaks was an avid support of Ceci Mahar (D) State Senator who voted FOR Bill HB5002 to destroy our local zoning laws.
This nonsense local political narrative Mr. Rosenwaks is playing in his campaign is insulting. We work together as Westporter’s to solve problems, no R, no D, we have one letter in common “W” and that is Westport.
Do we engage in debate? Yes, it’s called Democracy and it’s all part of listening, and speaking up.
Mr. Rosenwaks couldn’t even speak up for his own kids school (LLES) during any of the 60 plus meetings.
I am dumbfounded why any LLES parent would back someone like Mr, Rosenwaks, who never had the back of their kids as an RTM 6 District Member during these contentious meetings.
Leadership is speaking up….and sometimes you have to take hit or two….it’s part of participating as an elected volunteer official.
I hope everyone realizes our town has always had spirited debate dating back to the acquisition of Longshore to YMCA at Mahakeno.
These debates have never been political. These debates are always transparent, they are long, they are contentious, and they have always been decided by the voice of the people.
Leadership doesn’t come from someone telling you everything you want hear from a coffee shop or cafe’. Leadership comes from participating in the process and leading the process.
I was not going to do this Jimmy but here it goes:
Your Trumpian and divisive politics is not what we need in Westport!
Your own father allowed people with MAGA hats on to work at his nursery and called me a , ” commie, bitch, Marxist snot” for saying it was divisive for customers to see.
You yourself used a Trumpian derogatory and instigating nickname for David.
We do not need or welcome Trumpian type politics in Westport, period.
Ms. Frankel, Jimmy and I have known each other for 40 plus years..We occasionally butt heads for sure. But I can tell you that his father never owned a nursery..
My mistake then. Who owns Izzos?
Dave, thank you for clarification my friend!
TDS alive and well in Westport
One more reply to Jimmy,
Would you actually say that to David’s wife or children? . I think your rhetoric is why I am becoming even more of an Independent voter.
Hi Jimmy
Guess that’s the “hit or two” you spoke about.🤣
But she unknowingly complimented you as well.
Please Don’t respond to her rant 🔥
Happy Halloween 🎃 👻
Hi Tom,
I have no reason to my friend. I hope you are well, and family healthy. Happy Halloween to you as well!
Yes — David Rosenwaks is the strongest representative for the Democratic Party.
He’s a courageous leader with a clear strategic vision, strong collaboration skills, and a focus on planning and results. Rosenwaks brings the kind of thoughtful, forward-looking leadership that will truly advance Democratic Party values and priorities.
And if you thought party doesn’t matter locally, the Republican’s much touted ICE gestapo just raided a car wash in Hamden this morning. It was reported that among those taken was a young couple, leaving behind their two young children who were in school.
Outrageously immoral and disgusting, and anyone who votes for a Republican ticket is complicit.