By Gretchen Webster

WESTPORT–Westport is a Democratic town in a very blue state. There were 7,955 registered Democrats, 3,340 registered Republicans and 7,852 registered as other or undeclared as of Oct. 21, according to Voter Checklist, the online tool that Deborah Greenberg, the Registrar Of Voters, uses to track Westport voter registration.

In Connecticut, there were almost double the number of Democrats to Republicans – 901,000 Democrats to 525,000 Republicans registered in the state in November 2024, according to the Connecticut Secretary of State’s records.  State-wide, there are more other or unaffiliated voters, 1,105,000, than even the Democrats.

Yet in Westport, the last three first selectmen races were won by Republicans: Jennifer Tooker in 2021 and Jim Marpe in 2013 and 2017. This election year, the selectman’s race is even more complicated politically.

Democrat Kevin Christie is running on the Democratic ticket.  Don O’Day, who until recently was a registered Democrat, currently is endorsed by the Republican party and now is registered as an unaffiliated voter. David Rosenwaks, a third-party candidate and also a former Democrat, is registered with the Independent Party. He was also endorsed by The Forward Party, a “centrist party,” according to its website.

In addition to the unusual political background of the trio of selectmen candidates this year, it could become even more complicated if Rosenwaks wins, according to Town Clerk Jeffery Dunkerton, because Rosenwaks does not have a running mate. If he were to become first selectman, his opponents, Christie and O’ Day, would become the second and third members of the Board of Selectmen. The new board would be comprised of the three men now vying for the town’s top office.

Despite their various political affiliations, the three first selectmen candidates did agree on some issues during several forums held by various town organizations during this election season. Now, with the election about a week away on Nov. 4, Westport Journal is asking all three candidates some questions that may not have been answered during this election season:

Question 1: There seem to be stores and businesses continuing to close in Westport in the last few years – Mexicue and the Pancake House open only for two years, Bond Vet for less than that, and the large Patagonia building at the corner of Church Lane and Main Street vacant for nearly two years. As first selectman what do you propose to do to help the business community thrive in Westport?

Kevin Christie: Our local business community is a big part of what makes Westport thrive, and Amy and I will champion local businesses. We will evaluate creating the role of Director of Economic and Community Development, a position that Fairfield has employed to great success. Business and community concerns are intertwined, and both benefit when there’s someone dedicated to building consensus on how to move forward and facilitating those outcomes. We can add transportation issues to this position’s portfolio so that parking and traffic implications are also considered.

This extends beyond our downtown local businesses. We’ll collaborate with merchants and associations to strengthen Main Street, Saugatuck, and all commercial districts. And when state-led projects, such as Post Road construction, disrupt local businesses, we will work directly with the Department of Transportation and our state delegation to advocate for better coordination, clearer communication, and faster progress.

Don O’Day: This question assumes closures signal a town-wide failure. In reality, restaurant and retail turnover is common everywhere. Nationally, roughly 25% of new restaurants fail in the first year and about 50% within five years. Business outcomes depend heavily on individual models and market fit, not town policy.

That said, Don and Andrea believe Westport must remain a place where businesses can succeed. As First Selectman and Second Selectwoman, we will ensure permitting processes stay efficient, predictable, fair and never unnecessarily burdensome. We will regularly engage with business owners to understand challenges firsthand and address issues such as accessibility, parking, and customer traffic.

While no administration can guarantee the success of every venture, we will maintain a business-friendly environment, support smart growth, and remove avoidable obstacles. 

David Rosenwaks: As first selectman, I see Westport as more than a town. I see it as a destination for residents, neighboring communities, and visitors alike. But to get there, we can’t just tackle issues one at a time and hope for the best. We need government, merchants, and residents working together, truly together, to define what makes Westport a destination and how it benefits everyone while preserving our town’s rich heritage.  I recently watched a very inspiring video on YouTube from 1985 called “The Wonderful World of Westport.” I want a downtown that thrives and is bustling with energy, and I want every business scattered throughout the town to benefit from a sense of community and a shared vision for the future.

Merchants face high costs from high property values. Our vision can offset that by driving more patrons and boosting revenue. Success isn’t just about parking (which is important), but it’s also about creating strategies that grow business while protecting our heritage. That means positioning Westport as a destination.  We need vision, strategy, action, and results all delivered with urgency and collaboration. When everyone has ownership of the plan, we all win.

Question 2: Transparency seems to be a problem in the current administration. Would you encourage the meetings of town bodies to be streamed and recorded? And how would you provide a path for constituents to communicate with the first selectman?

Don O’Day: We disagree with the premise that transparency has been lacking. Often, dissatisfaction with an outcome is labeled as a transparency issue, even when processes were open and fully transparent. 

However, we agree that communication can always improve and under our leadership, it will.

Our record shows that. When Don chaired the Coleytown Middle School Building Committee, he led regular, clear public updates throughout difficult moments — a level of transparency that earned broad community trust and an Unsung Hero nomination.

As selectmen, we will:

• Expand livestreaming and recording of meetings within our jurisdiction.
• Develop a clear media and IT plan with our Director of Information Technology.

Leadership means listening, communicating clearly, making decisions for the greater good — and standing by them. That will define the O’Day–Moore administration.

David Rosenwaks: Effective leadership, to me, is built on three fundamentals: Transparency in government, effective communication channels, and holding ourselves accountable for results. What sets me apart, and makes me the best candidate for first selectman, are these values. They reflect who I am and what I stand for. I am the first-ever Independent Party-endorsed candidate in Westport’s history and authentically represent the interests of our residents. For me, the community is my party affiliation.

Yes, I support streaming town meetings. Yes, I support direct communication between constituents and the First Selectman. I’ve been giving out my personal phone number to everyone I meet. I also propose a weekly recorded podcast where I interact with residents one-on-one. I am excited about hosting weekly brown bag lunches in town hall. I also propose district-based constituent committees to collaborate with me on vision, strategy, tactics, and budgets. I am uniquely the people’s representative.

Kevin Christie: The first selectman sets the tone and culture for Town Hall and the community. I start with the belief that government exists to support the people. Open government is about more than transparency. It’s about engagement, accessibility, and trust. I’ll make openness and responsiveness part of how Westport operates every day, from how we communicate to how we collaborate.

That means going beyond streaming and recording meetings and posting meeting packets online, though all of that should happen, and Board of Selectmen packets should certainly be posted (typically, they are not). Amy and I will continue our open “Coffee and Conversation” sessions, including evening versions, to keep residents directly engaged in priorities and decisions. I will remain accessible by phone and email, and we’ll continue to find new ways to make Westporters aware of town projects earlier in the process so more people can participate meaningfully.

Question 3: The first selectman has a large number of direct reports. There is a lot of highly-skilled talent in Town Hall from a very wide range of functions. What in your background prepares you for being an effective overseer of such a diverse number of departments such as Police, Human Services, Conservation and Assessor? What is your plan for retaining that talent, with little control over their pay and benefits?

David Rosenwaks: Retaining talent in Westport, where the town has little control over pay or benefits, starts with inclusion and belonging, grows through vision and strategy, and is solidified by trust and confidence. These elements will be a priority in my administration.

Inclusion is straightforward, but true belonging requires empathy and outreach that create a visceral connection with the Westport brand. This is achieved through a shared vision and proactive long-range strategy. When our diverse departments collaborate to shape the town’s future, it ignites ownership and commitment. Differences fade, and unified intention takes center stage. When employees feel involved, respected, and appreciated, trust and confidence in leadership flourish.  This is how I approached leadership in my banking career, and how I built a successful asset management firm from scratch.  Gaining trust from business partners, partner banks and investors is what I’ve always done.  Building genuine connections based on trust and open, honest dialogue. 

Through my work on the RTM, RTM committees, Westport Arts Advisory Committee, the PTA Council, and regularly attending meetings of every kind, I have developed strong relationships with town employees within town hall as well as many members of our Police and Fire departments.  By being a servant leader to my constituents in District 6 and beyond, I have helped many citizens solve their one-off situations and issues. In the process, I have already interacted and formed solid connections based on trust with many town employees.

Westport is teeming with highly-skilled talent across many departments and services. The hallmark of effective leadership is not content management—it is context leadership. A strong leader unites departments under a shared vision and strategy that maximizes the town’s potential. Good leaders ask questions, listen, and inspire; they do not rely on flawed experience or personal opinions. Leadership requires authenticity, credibility, vision, and trust.

I am uniquely qualified to lead in this way. Unlike my opponents, I focus on these leadership qualities and call for a complete change in direction. Others may talk about collaboration or non-partisan advocacy, but talk alone cannot re-inspire our government or refocus its efforts. I have consistently represented my beliefs and will continue to do so, drawing on executive experience built through humility and example—not flawed experience or indecision.

Kevin Christie: This role is more than management. It’s leadership. The first selectman is Westport’s chief advocate and representative, responsible for setting the tone and culture that allows talented employees to do their best work in service to our community. Strong management skills are essential, and I bring that experience from a 15+ year career in finance, investment banking and strategy, leading teams and executing complex transactions amounting to over 80 times the value of the town’s current $500 million laundry list of capital projects. A critical part of my success was motivating and supporting my teams.

Great leadership, and management as part of it, is about bringing people together around a positive vision, listening, empowering, and ensuring people feel heard and valued. I will continue to build on my relationships with our town staff, and further strengthen collaboration and trust. The first selectmen may come and go, but our dedicated employees remain. My job is to help them succeed on behalf of the community they serve.

Don O’Day: This is a very important question and is the key differentiator in the race for selectmen.  Being first selectman is, above all, a management job.  It is a job for proven leaders with extensive resumes.

Don O’Day’s 40-year career, including as a senior executive and a Residential Lending CFO at Citigroup, involved managing large teams, multiple direct reports, and complex operations at a scale that is consistent with the oversight required at Town Hall. Andrea Moore is our current second selectwoman. She has led significant town bodies, including her work as the vice chair of the Board of Finance and major community initiatives. Together, we are the only ticket with a demonstrated record of leading high-stakes public processes to successful outcomes in Westport.

Finally, employee retention is not only about salary; it’s about leadership. People stay when they’re respected, supported, challenged, held accountable, and appreciated. Our leadership model is clear: set high expectations, ensure people know their roles, provide feedback, empower them to succeed, and recognize their contributions. That is how we’ve built strong teams before — and that is how we will lead Town Hall.

Question 4: Why does it take so long for town projects to be brought to fruition in Westport? New restaurants and new business owners complain all the time that it takes forever to get approvals in Westport.  And even when it appears the town is working on a concept – like improving Parker Harding, for example, you can find news stories from the 1960s, ’70s and ’80s saying the town is addressing exactly the same issues now that they were then. What can be done to change all these delays?

Kevin Christie: What can be done? Elect Kevin and Amy. My professional background has been all about leading teams to solve complex challenges and deliver results. As First Selectman, I’ll bring that same focus to Westport.

For any project, whether it’s Parker Harding or something else, we first need to clearly define the problem we’re trying to solve. The decision-making process must include public input, which we will proactively seek, and it must certainly include input from our subject-matter experts in town departments and our elected and appointed boards, commissions, and committees. Once we understand the options and consequences, decisions need to be made and acted on. Amy and I are prepared to do exactly that.

Our community deserves progress, not decades of studies and reports without implementation. We will bring focus, coordination, and accountability to move projects forward and improve quality of life for Westporters.

Don O’Day: Westport has checks and balances by design. Independent bodies like the Planning & Zoning Commission, Board of Finance, and Board of Education do not report to the first selectman — and that’s appropriate. But checks and balances must not be an excuse for needless delays, and leadership is about managing in a complex structure.

We’ve already proven Westport can move quickly. During COVID, the administration and P&Z collaborated effectively to support local businesses — demonstrating that urgency plus alignment and teamwork equals action.  It is remarkable what can happen when people work together.

As first selectmen, we will:

• Bring stakeholders together earlier
• Establish clear timelines and accountability
• Improve clarity so businesses understand the process from the start
• Recommend procedural streamlining when it doesn’t compromise public input or safety

Not every outcome will satisfy every interest, but decisions must be timely, informed, and well communicated. We know how to build consensus, move projects forward, and not allow progress to be stalled by a loud minority. We will apply that discipline to drive results for Westport.

David Rosenwaks: The same level of thinking will not produce different results. I am the only candidate seeking a significant change in Westport’s approach to governing and leading. My opponents are wrapped up in experience, what they know, where they participate, all of which leads to status quo thinking and delayed results. Leadership matters, not just experience. Without a shift in the leadership context, our government will remain mired in tactical ineffectiveness.

We must embrace the power and influence of our residents. That means engaging them from the start; not just the loudest voices, but every voice that wants to be heard.

Westport needs a fresh, non-traditional approach to leadership. Bureaucrats cannot drive fast, meaningful progress. If we rely on the same people, the same experience, and the same approach, we will not achieve comprehensive, timely results. We must identify bottlenecks and define a new approach to process, procedure and regulation.

We need a leader who is not bound by bureaucracy, not focused on opinion, and not impressed by experience alone. I lead through involvement, vision, and strategy—turning each into actionable plans and measurable results. Always open, always transparent, always accountable.

Correction: an earlier version of this article misreported the dates of Jim Marpe’s elections to First Selectman.