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.
Ten years ago, while snowed-in at her mother-in-law’s house in Fargo, North Dakota, Kline noticed her son reading an unfamiliar book: “Centuries of Stories.”
In “The Incredibly Human Henson Blayze,” Henson is a Black 13-year-old football powerhouse in a small town of mostly white residents, and an ugly, racist past. The townsfolk excitedly follow his progress, and are thrilled to have their token African American All-Star-to-be.
