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’ve asked the men and women running for 3 important boards — Selectmen/women, Planning & Zoning, and Education — one specific question.
We’ve printed their responses verbatim.
This week’s question — the final one in this series — for the Board of Selectmen/women is:
This is your chance to send your message to Westport voters – to seal the deal. What do you want them to know about you, your plans, and yourselves? Go for it!
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Democratic Party-endorsed candidates Kevin Christie and Amy Wistreich say:
Over the past few months we’ve knocked on doors, talked with voters, and met neighbors at community events and coffee chats. What we’ve heard from Westporters is clear. People want three things from their next leaders:
- A clear vision for Westport,
- A thoughtful plan that reflects the needs and priorities of the community, and
- The proven ability to execute and get things done the right way.
That is exactly what Amy and I bring to Westport.
Kevin Christie and Amy Wistreich.
Vision
We will be leaders and advocates for all Westporters, listening carefully, communicating clearly, and representing the entire community.
Our vision is a Westport that continues to lead in fiscal discipline, education, quality of life, and environmental sustainability. Imagine a Westport where local businesses thrive and downtown parking is finally resolved, where there are more opportunities for seniors, teachers, and first responders to live in the town they love, where Saugatuck has development that works for Westporters, and where kids can safely walk or bike to school.
We see a town that protects its shoreline, open spaces, and trees, not just for today but for generations to come. We see a government that is open, transparent, and inclusive, where every Westporter feels heard and respected.
That is our vision, because leadership means more than managing what is in front of us. It is about shaping what comes next.
Planning
Vision only matters if it is matched with disciplined, collaborative planning. We will manage with fiscal responsibility and transparency, ensuring that Westport’s half-billion-dollar capital forecast reflects community priorities, not wish lists.
We will break the cycle of “study and shelve” spending by setting clear priorities, relying on experts, and remaining accountable. We will protect Westport’s AAA bond rating through long-term planning, not short-term fixes.
We will work with state and federal partners, including the Department of Transportation and our Westport delegation in Hartford, to secure funding and move long-delayed projects forward. Westport deserves leaders who pick up the phone (unlike the DOT maintenance facility project), build relationships, and turn partnerships into results.
We will plan responsibly by supporting smart development that protects our environment and expands housing options for the people who make our town work. We will strengthen local businesses, simplify the permitting process, and ensure downtown and Saugatuck remain thriving economic and cultural centers.
That is what thoughtful, community-driven planning looks like.
Execution
Great plans only matter if you can deliver. Nothing gets done without teamwork.
With more than 15 years of professional experience in finance, investment banking and strategy at IBM, Merrill Lynch, Bank of America Merrill Lynch, and the Madison Square Garden Company, I have successfully led teams and executed complex transactions amounting to more than 80 times the value of the town’s current $500 million list of capital projects.
Amy’s public service on the Zoning Board of Appeals and the Planning & Zoning Commission, along with professional experience in land use, architecture and construction, means she knows how to ask the right questions, evaluate details, and move projects forward.
Our combination of experience is unmatched.
We will prioritize finishing Long Lots/Stepping Stones on time and on budget, completing a practical downtown redesign that improves safety and parking, addressing flooding and climate resilience, and creating a town-wide plan for maintaining athletic fields, sidewalks, and public spaces.
We will turn plans into action through collaboration, transparency and accountability.
Westport is special because of the people in our community. Amy and I are proud Democrats and proud Westporters. We have the vision, the plan, and the proven experience to execute, and with you we can get things done together.
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Republican Party-endorsed candidates Don O’Day and Andrea Moore say:
Westport is about to hire its next leadership team, and experience matters, particularly on day one.
Since July, Andrea Moore and I have had the privilege of meeting thousands of you, listening to your hopes for Westport, and sharing a simple truth: Leadership is about more than hearing your concerns. It is about having the proven ability to act on them. It is about standing tall and taking a stand for the greater good of our town.
The O’Day Moore team does just that.
Andrea Moore and Don O’Day.
Let me tell you about Andrea Moore.
Andrea is Westport’s current second selectwoman, and has been my superpower in this race. A lifelong Westporter, she has served at every level of community leadership, from senior PTA roles to vice chair of the Board of Finance and as a trustee of the Westport Weston Family YMCA.
In her more than 20-year financial services career, she led complex teams and made tough decisions. In her current role, she has appointed nearly 100 residents to boards and commissions, ensuring Westport’s government is filled with talented, civic-minded volunteers. She knows our people. She knows our process. She knows how to get things done.
No one knows Westport more than Andrea Moore, and no one is more ready to keep leading it forward.
My story in Westport began 31 years ago, when my wife Toni and I stretched to buy a home here and raise our 3 sons. Professionally I spent 35 years in financial management at Citi, including as a chief financial officer in our residential lending business. I have led organizations larger than Westport’s municipal workforce. Managing complex teams and budgets is not new to me. It is what I do.
Westport has regularly placed its trust in me. I was twice elected to the Board of Education, and was chair for 4 years.
I led our schools through the 2008 to 2010 financial crisis. When districts nationwide were slashing budgets, I led with clarity, transparency and precision — cutting where we could and protecting what mattered most.
Later, when Coleytown Middle School was shuttered, I was asked to lead the rebuilding effort. I communicated clearly at every step, earning broad praise for transparency and results.
Today, as a member of the Representative Town Meeting (RTM) and Long Lots School Building Committee, I led a plan for a new school that earned unanimous approval across every board, including Planning & Zoning.
Andrea and I have been tested, and we have delivered.
So why O’Day/Moore?
Because Westport is choosing between those who have already led this town through crisis, budgets, rebuilding and complex governance, and those who have not.
Listening is essential. But leadership means deciding, especially when 2 groups want opposite things. If you avoid criticism by avoiding decisions, you are not leading — you are taking a poll.
We will always listen and we will lead, anchored in facts, transparency.
Our Immediate Priorities:
- Fix infrastructure now, including a solution for Coleytown Elementary, downtown improvements, and upgrades at Longshore.
- Protect Saugatuck with responsible development, supporting scaled, reasonable projects instead of a massive housing plan without full Planning & Zoning oversight.
- Make Westport safer and easier to get around, with more sidewalks, marked bike lanes, better enforcement including cameras, and smart traffic light timing.
Andrea and I are ready to serve. Westport deserves leadership with a proven record of solving problems, managing teams, rebuilding schools, balancing budgets, and earning town-wide trust.
Experience matters, especially on day one.
We ask for your support, your confidence, and your vote.
Thank you for your kindness throughout this journey. We look forward to leading Westport forward.
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Independent Party-endorsed candidate David Rosenwaks says:
The inspiration behind my decision to enter the first selectman race comes from a simple belief: Westport deserves a different kind of leadership. Leadership that’s independent, inclusive, and grounded in collaboration.
What truly sets me apart are the values I live by every day — outreach, listening, empathy and inclusion. My goal is to unite our shared vision for Westport and work together to respect the heritage that got us to this point, while also enhancing the assets of our beautiful town. These values will guide every decision I make from day one.
David Rosenwaks and family.
As a member of the Representative Town Meeting (RTM), I’ve seen firsthand the need for something our town has never truly had: a long-term, strategic plan that defines our vision, aligns our goals, and ensures that every decision we make supports our future, not just the moment. With collaboration and transparency, we can focus on initiatives with the greatest impact and return on investment. I am committed to delivering Westport’s first comprehensive strategic plan by April 1, 2026.
With a clear plan and strong leadership values, we can transform how Westport governs and budgets. Imagine a budget process guided by purpose from the very start where priorities, projects, and expenditures align naturally because we’ve already done the hard work of planning together in a holistic fashion.
My approach is simple: engage every department, listen to every voice, and lead through collaboration. It’s not the easiest path, but it’s the right one; and it’s the one I’m uniquely prepared to take as your next first selectman.
Running as the first-ever Independent Party-endorsed candidate in Westport’s history allows me to lead free from partisanship, to put people and progress first.
My candidacy also creates a unique opportunity to bring everyone together. Per the Town Charter, both the Republican and Democratic candidates could serve on the Board of Selectmen alongside me in the case I am elected as first selectman.
We can build a leadership team that includes all voices and all ideas, and I argue such a Board of Selectmen represents a more perfect union. Every member goes into every conversation with an open mind ready to listen, deliberate and be decisive based on all our constituents’ voices. That’s what collaboration looks like in action, and the kind of government Westport deserves.
My promises to you as your First Selectman:
- I will prioritize the voices of our community making sure everyone is heard, not just the loudest or most powerful.
- I will lead with full transparency and accountability.
- I will protect the heritage of our town and the quality of life we all cherish, always standing for Westport at both the state and local level.
- I will keep our housing market strong by balancing smart spending with responsible taxation, working closely with the Board of Finance.
- I will support our schools and lead a full infrastructure review, always planning and budgeting in partnership with the Board of Education.
- I will strengthen our most important relationships with the Connecticut Department of Transportation, state leaders, and local housing developers to advance our interests and keep Westport moving forward.
- And I will act, collaboratively and decisively, on our most critical issues: affordable housing, Saugatuck development, downtown parking, Cribari Bridge, community gardens, and traffic congestion.
At a time when civic discourse feels fractured and challenges seem bigger than ever, Westport deserves leadership that brings people together: inclusive, strategic, fiscally responsible, transparent and accountable.
I believe in value-driven leadership that pairs long-term vision with short-term action. I believe in collaboration over partisanship. I believe in urgency, accountability, and progress that you can see and feel.
Your voice. Your town. Your government.
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For last week’s “Where We Stand” responses, click here.
For the third “Where We Stand” responses, click here.
For the second “Where we Stand” question, click here.
For our first “Where We Stand” question, click here.
