“Where We Stand”: Selectman Candidates On 10-Year Capital Plan

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’re asking 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:

The 10-year Capital Plan is lengthy, and expensive. What are your top 5 priorities – and why?

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Republican Party-endorsed candidates Don O’Day and Andrea Moore say:

Westport’s current 10-year Capital Plan includes more than $400 million in proposed spending for town and school projects, not including interest on the debt. This is in addition to prior capital spending totaling $108 million, also excluding interest.

Despite this significant forecast, Westport recently received an exceptionally strong credit rating, reflecting the disciplined fiscal management of the administration, the Board of Finance, and RTM. This excellent rating helps lower our borrowing costs, allowing Westport to advance our Capital Plan efficiently and responsibly.

That said, the 10-year Capital Plan must and will be carefully re-evaluated when we take office in November.

Andrea Moore and Don O’Day

Important questions:

1. What are our current capital spending priorities?
2. How will we evaluate each item in the plan?

Our Capital Priorities

We have identified 3 projects that are long overdue and will be prioritized:

1. Parker Harding Plaza – the current estimate is ~ $6 million.

The current estimate reflects a full redesign of the entire plaza and parking lot. Our immediate focus will be bringing the parking lot up to code. This will reduce the number of spaces in order to address safety and accessibility requirements. We will identify replacement parking spaces before proceeding with paving and steps to find these spaces are underway. A new parking structure in the Baldwin Lot will be an option if needed.

2. Longshore facilities – the current estimate is ~ $14 million (shed, Clubhouse, cart barn parking and surrounding area – more is planned)

The Longshore redevelopment includes our private/public partnership with the Inn at Longshore and Delamar. The first priority in the Longshore development plan is replacing the maintenance facility. While the exact size, location and specific design of the shed can be debated, the need to replace the shed is clear.

The Clubhouse at Longshore also requires immediate attention, as its current condition limits revenue potential and does not reflect the quality of one of Westport’s most valued recreational assets. Longshore is a centerpiece of Westport’s recreational offerings, and improving these facilities ensures safe, enjoyable experiences for residents of all ages.

3. Coleytown Elementary School – the current estimate is $85 million

CES is significantly overdue for replacement or major renovation. Recent roof leaks forced the closure of a kindergarten class, highlighting the urgency. Planning for CES must begin immediately, even as Long Lots and Stepping Stones construction proceeds. Westport must be able to advance multiple major projects simultaneously, and CES is too important to defer. Investing in the school safeguards the learning environment and future success of our children.

Other critical projects requiring full attention include a combined police, fire, and EMS facility, as well as flood resiliency and bridge projects.

Evaluating the Capital Plan

Once in office, we will work with the finance director, the Board of Finance, the RTM and project sponsors to review every line item in the Capital Plan. Each project will be assessed and prioritized as high, medium or low based on safety, urgency, operational need, cost escalation risk and community benefit.

This process will not be a one-time exercise. It will become part of a disciplined, transparent, annual capital forecast process to ensure Westport invests wisely and delivers results for residents. We will make every dollar of taxpayer investment count.

Looking Ahead

We must ensure that our taxes remain competitive compared to other towns in Connecticut.  It is a source of strength and adds to our property values.

By focusing on urgent needs, rigorously evaluating all projects, and maintaining transparency, we will ensure that Westport continues to thrive while managing its resources responsibly.

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Independent Party-endorsed candidate David Rosenwaks says:

With more than 250 line-item capital requests presented in random order and spread over a decade, it’s difficult for all of us to grasp the logic, purpose, or prioritization behind this almost $500 million plan.

Quite frankly, I’m surprised by the lack of strategy, rationale and fiscal discipline. If we were to follow this plan as written, taxpayers could face up to a 20% increase in taxes solely due to capital expenditures. I’m perplexed by how we’ve moved from a fiscally responsible approach with stable tax rates to a proposal that would significantly burden our residents.

David Rosenwaks

Westport is at an inflection point. We can continue managing from crisis to crisis, or we can pivot to a higher level of proactive planning and proficient management. I will lead with a different approach, one that produces results through vision, strategy, and disciplined execution. My thoughts and priorities are as follows:

1. Deliver a Strategic Plan

My first priority, as your first selectman, will be to launch a comprehensive, long-range strategic planning process for the town, one that aligns our initiatives, priorities and expenditures. My commitment is to have this plan completed by the end of Q1 2026.

This plan will guide our long-term tactics, including capital investments, and provide a framework for annual budget decisions. It will engage all major town bodies — the Board of Education, Board of Finance, Planning & Zoning Commission  — to assess critical issues, identify opportunities, and establish a shared vision built on clear strategic pillars. Throughout this process, residents will have full transparency and an active voice.

2. Performance and ROI

My second priority is to ensure every initiative is clearly defined, categorized, and measured for performance. We will apply proficiency and ROI metrics to make certain every tax dollar is spent wisely and delivers measurable results. My commitment is to uphold the highest standards of efficiency, effectiveness and accountability in every expenditure. This disciplined approach will allow us to evaluate initiatives and alternative approaches using clear, comparative data.

3. Informed Prioritization

With a solid strategic framework and clear performance metrics in place, we can make smart, deliberate choices about which initiatives are essential and which can wait. We will know what initiatives provide the most immediate, most cost-effective impact.  Your voice will guide these decisions — it’s about your voice, your town, your government and your choice.

4. Guiding Principles

Our guiding principles should set our strategic priorities; be straightforward and enduring:

• Safety: Support police, fire, traffic and infrastructure to provide a secure environment for all residents.
• Schools: Preserve our most valuable asset, our schools, both academically and structurally, avoiding crisis-driven repairs.
• Smart and Sustainable Development: Support thoughtful growth that enhances our community’s architecture and heritage, while proactively addressing environmental concerns.
• Parking Concerns: Support residents and merchants alike.
• Essential and Recreational Services: Enhance the quality of life of all members of the community.

5. Leadership with Purpose

It would be easy to simply dictate a list of capital priorities; but that’s not effective leadership. My approach is strategic, inclusive, and purpose-driven. My commitment is action and results, guided by passion for this community and a shared purpose to make Westport stronger, more sustainable, and more connected.

What matters most are not the ideas I impose, but my ability to lead and unify our values, interests, and priorities. By hearing every voice, I will find our common ground. I will not seek differences, but rather areas where we can align and collaborate. It is not each of our ideologies against one another, it is all of us together protecting the quality of life, the essence of our town, and the value of our tax dollars.

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Democratic Party-endorsed candidates Kevin Christie and Amy Wistreich say:

The 10-Year Capital Plan is a management tool, not a substitute for a vision for Westport.

Right now, it’s a $500 million wish list of nearly 300 projects submitted by town departments, including 67 estimated to cost $1 million or more. Items range from $65,000 for a sewer pump station generator to $92.5 million for a combined police, fire and EMS headquarters.

The job of the Town’s CEO is not simply to manage the list in conjunction with the superintendent of schools. It’s to understand Westport’s needs and provide the leadership, vision and discipline to set priorities, and ask what’s missing.

Kevin Christie and Amy Wistreich.

As your selectmen, we will:

Lead the process. Use the forecast not as a to-do list, but as an opportunity to prioritize projects based on how they fit into a larger strategy for Westport. That means launching a full review of the forecast, collaborating with the Board of Finance, RTM, Board of Education and the public so that the order in which we tackle projects reflects what Westport needs, what we can afford, and ensures things are done properly, on time, and on budget.

Be fiscally responsible. The capital plan is funded by your tax dollars. We take that responsibility seriously and will spend wisely and only when necessary. That means no wasteful studies, and no $7 million maintenance facility in the middle of Longshore’s golf course.

Balance wants with needs. Westporters want the town to be more active, walkable and bikeable. They also want our recreational facilities and playing fields better maintained. Priorities like these aren’t fully reflected in the forecast today. We can change that.

We come to the selectmen’s office prepared for this. On the Board of Education’s Finance and Facilities Committee, I helped develop the criteria to prioritize our school district’s capital needs after witnessing the mold issues at Coleytown Middle School and Long Lots Elementary.

The BOE’s and superintendent’s focus has been on infrastructure: keeping our buildings dry and maintaining air quality by investing in the building envelope and mechanicals, and these are reflected in the forecast. We’ve seen what happens when those aren’t prioritized: costly renovations and new construction. That’s a lesson I’ll carry to Town Hall.

Our current roles on the Board of Education and Planning & Zoning Commission give us comprehensive insight into the areas that need the most attention. With this, plus what we have learned during our campaign in talking to Westporters, town staff, board and commission members, and local businesses, we’re prepared with a preliminary list of our investment priorities, focused on our infrastructure. They include:

• Fixing the problems that have taken too long: including Parker Harding and downtown parking.
• Schools: We’re committed to ensuring that Long Lots/Stepping Stones comes in on time and on budget, planning ahead for Coleytown Elementary, and maintaining our schools to extend their useful lives.
• Efficiency: Ending the cycle of “study and shelve” spending by using local expertise to act. 
• Sustainability: Flood resiliency, and preserving open space when considering projects, including a sensible solution for the Parks & Recreation Department maintenance facility that protects the golf course at Longshore.
• Securing grants: Aggressively explore state and federal funding and resources to support projects while reducing taxpayer burdens.

Together we bring decades of experience in finance, corporate strategy, land use, and construction. We know how to manage risk, sequence and execute complex projects, and ask the right questions before the taxpayer foots the bill.

Fiscal responsibility isn’t just about cutting costs. It’s about making smart, transparent, and forward-looking decisions — informed by our community — that strengthen Westport and respect both taxpayers and tax dollars.

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To read last week’s “Where We Stand” responses, click here.

For the second  “Where we Stand” question, click here.

For our first “Where We Stand” question, click here.