This week, “06880” introduced a new feature: “Where We Stand.”
Once a week between now and Election Day, we’ll ask candidates for 3 important boards — Selectmen/women, Planning & Zoning, and Education — one specific question.
We’ll print their responses verbatim.
An informed electorate is the greatest bulwark of democracy. Westporters have always participated avidly in our town government.
“06880” is proud to do our part this fall to help.
This week’s question for the Board of Education candidates is: “What is the single most important issue facing Westport Public Schools right now, and how will you address it?”
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Republican Party-endorsed candidates Dorie Hordon (incumbent), Michelle Hopson, Andy Frankel and Kaitlin Zucaro say:
The biggest issue facing Westport Public Schools right now isn’t test scores, facilities, the budget, or even athletic coaches — it’s leadership.
Without strong, effective leadership and direction, everything else meanders and slips. And right now, our Board of Education badly needs members who offer direction, vision, initiative and insight, and have a willingness and capacity to speak up and contribute.
That’s why we’re running. It’s time for fresh leadership that puts the preparation of students first, and restores focus on a clear mission for student success. We bring the wide-ranging experience needed for effective governance of our school system. Among the 4 of us, we have worked as highly accomplished educators, finance and marketing executives, technologists, and big-firm lawyers.
From left: Michelle Hopson, Dorie Hordon, Kaitlin Zucaro, Andy Frankel.
We also know our schools at every level — elementary, middle and high school. Collectively, we have 8 kids currently enrolled in Westport public schools (plus 4 graduates). Not one of the current Board members (other than vice chair Dorie Hordon from our slate) has any kids in our schools.
We bring a voice for parents of current students. That personal connection also makes us deeply invested in student success.
Our mission is simple: return the focus of the board and administration to the success of Westport students through effective leadership, accountability, and emphasis on the right priorities.
Those priorities include:
Academic excellence. We’ll work to make Westport schools among the best in the nation by staying focused on fundamentals, fostering critical thinking, and preparing kids for a changing world, especially with the advent of AI. Despite relatively high state rankings and standardized test scores, we are falling behind peer school districts in key areas. We have also heard from multiple families with serious concerns with the administration of special education. We can clearly do better, and should strive to ensure that all of our students are ready to succeed.
Importantly, a focus on academic excellence does not mean sacrificing athletics, the arts and other valuable extracurricular activities. Our athletic programs are among the best in the state, yet the board has provided little guidance and leadership even for easily solvable problems, illustrated by the fact that Staples has no girls locker room for girls sports teams, and most fields lack lights for nighttime practices and games.
Smart and transparent budgeting. Westport schools cost taxpayers more than $150 million a year — over 60% of the entire town budget. That’s a huge investment, and families deserve transparency and efficiency. We’ll make sure resources go where they matter most.
Real oversight. Rubber-stamp boards don’t serve families. We’ll ask hard questions, hold the administration accountable, and look for creative solutions. The oversight of a board shouldn’t be about threatening administrators when you don’t get your way on any particular issue; it’s about making sure every decision stands up to scrutiny and serves students well.
Safe, modern schools. Kids need secure, well-maintained, and tech-ready facilities to learn at their best. We’ll ensure Westport schools keep pace with the demands of today’s classrooms and tomorrow’s challenges.
Westport schools are a crown jewel of our town. But that reputation can’t be taken for granted. It takes leadership to maintain a premier district and push it forward. That’s why we are running. We bring different backgrounds — education, law, technology, business — but we are first and foremost parents who share a common vision of strong schools supported by a strong community.
We offer independence, unity, a constructive approach, and a commitment to student success with one guiding principle: Every decision must serve the best interests of Westport’s students.
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Democratic Party-endorsed candidate Abby Tolan (incumbent) says:
Living through Coleytown’s shutdown, the combined middle schools, and COVID, as well as serving on the board, I’ve learned not to predict challenges or believe we will have the luxury to face one at a time. Even putting aside consideration of the inevitable surprises, we know our schools, like all others, must navigate a shifting landscape:
The integration of AI into schools is both an educational and moral endeavor. Our responsibility is to equip students to use technology thoughtfully and responsibly, without letting it replace the deep processes through which they learn. We must also incorporate strong soft skills into our program, which both research and day-to-day living confirm are both vital to success and increasingly lacking in graduates.
Our strategic plan addresses this dual challenge by creating a forward-facing, flexible program that balances technological fluency with human-centered growth. We must recognize technology’s potential while affirming the importance of human judgment, creativity, and compassion, producing graduates who are each prepared to contribute meaningfully to the future.
Abby Tolan
Our ever-increasing annual operating budget is a constant concern.. This community is unflagging in its support of our public schools, which benefits us all and for which we are grateful. But the education budget is a major portion of our municipal expenditures and we must find ways to control costs to sustainably balance fiscal responsibility and student achievement.
Our capital needs present opportunity, but require significant investment. We are building 2 new schools with Long Lots and Stepping Stones, and are preparing to undertake significant renovation of Coleytown Elementary. As a board, we work closely with our funding bodies to ensure that the most basic facilities needs – namely that schools are temperate and dry – are addressed. There are many other capital demands, and we must collaborate on a long-term capital improvement plan that serves both school and town-wide priorities.
I could go on, but my point is this: it is not a singular challenge we confront but rather a question of how the district, with the board acting as the governance team, responds.
What makes me hopeful is that I know how to do this work. As a professional in special education, I’ve spent my career weighing individual needs against broader program goals, listening carefully, and then making decisions that are both personalized and intentional. That perspective has been invaluable on the board, where every decision has ripple effects across classrooms, families, and the town as a whole. At the same time, we cannot lose sight of the needs and dreams of every child, lest we lose the tree for the forest.
The role of a board member is to discern what matters most for students and ensure the district has the structure, resources and direction to deliver. Sometimes that means stepping back and hearing every side of an issue. Sometimes it means making a hard call when there is no perfect answer. Always, it requires keeping students at the center of the conversation.
People will always disagree — that’s fair and expected — but even amid differing views, this board has achieved significant successes against current headwinds: increased student performance, new schools, security audit and plan, reduction in student out-placements, increased student voice, and again, I could go on.
The challenges will keep coming, and while we cannot choose which ones arrive, we can choose how we meet them: with expertise, open ears, courage, and a steady focus on preparing every student to thrive. I am committed to continuing the work to move our schools forward with innovation and humanity.
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Two other Democrats will be on the ballot as petitioning candidates, having secured over 400 signatures. Jodi Harris and Stephen Shackelford say:
Dan, thanks for this opportunity. Before going into what needs immediate attention, we want to call out what’s working: the dedicated teachers and staff of the Westport Public Schools and our generous force of parent volunteers. They all work together to support each other and, most importantly, the next generation of Westporters.
Simply put, the most important issue facing our schools is one of leadership. The Board of Education and the administration must use their roles and resources to address the concerns of every stakeholder. And they must do that efficiently, effectively, and transparently.
Stephen Shackelford and Jodi Harris
For some reason it is taking years to fix small problems, which become big problems, which in turn become seemingly intractable — and expensive — problems. In recent years, too many teachers and staff members have been held to a higher standard than the administrators they report to.
The administration’s role is to eliminate obstacles so our teachers and staff can succeed. The role of the BOE is twofold: to manage the superintendent, and to serve as the elected voices for our schools.
Yet in one meeting after another, the BOE is doing less and less to engage our superintendent in meaningful debate about what needs to improve and what he is getting right. If we don’t make smart decisions, we risk failing to attract the most talented educators and staff to our schools. Here are just a few recent examples:
Many elementary school teachers have desperately called for more paraprofessional support, yet last year’s budget proposal instead added additional assistant principals, expanding an already top-heavy organization without providing classroom support.
Additionally, a lack of substitute teachers means our educators are losing their prep periods to cover classes, a problem particularly noted at the middle-school level. The systemic issues extend beyond the classroom: A single overworked plumber services all 8schools, leading to long wait times for critical repairs. There are many more stories we don’t have room for here.
The School Climate Survey presented in September 2024 showed a troubling drop in student engagement. Where are the 2025 scores? Why haven’t they been presented? Parents and students deserve transparent reporting of the latest scores and a clear plan to address any issues. The north star for both the administration and the BOE is continuous improvement and a positive outcome for our students.
As board members, we’d take a different approach from that of many of the current members. The BOE must be proactive, not reactive, and be honest with our community. First, we’d directly engage with our teachers and staff. Do they feel adequately supported and respected? Why do they think hiring pools are shrinking so dramatically, and what changes do they think are critical for success in the classroom?
Next, we’d engage more purposefully with our students. For years the BOE has promised to survey Staples students for inside knowledge on their coursework, and to capture the pulse of student life — but it hasn’t happened. This needs to change immediately. Giving our students a voice and a forum for feedback is the least we can do. Good ideas can come from anywhere, and sometimes it’s as though our kids are actually the adults in the room.
It’s time for the BOE to stop making excuses, and start engaging and executing on solutions. We want to help move our schools from good to great — with transparency, accountability and accessibility at the forefront.
We need a board that is inclusive, not exclusive. We want to meet the needs of our students with the teachers, staffers, facilities and curriculum they deserve. And that starts with board members who understand and embrace the critical role they play.
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Robert Harrington (incumbent) was not endorsed for re-election by the Republican Town Committee. He is running as a write-in independent candidate. He says:
The single most important issue facing the Westport Public Schools today is accountability. Westport has long been recognized for academic excellence, a dedicated teaching staff, and strong community support. But excellence cannot be sustained without transparency, responsibility, and a willingness to ask hard questions. A district that fails to hold itself accountable risks losing the trust of students, families, and taxpayers — the very trust that underpins public education.
Parents and taxpayers deserve to know not only what decisions are being made, but also why those decisions are in the best interest of students. When boards or administrators simply “go along,” rubber-stamping pay raises, building projects, or investigations without scrutiny, the message is that convenience matters more than honesty. That is not acceptable in Westport.
Robert Harrington
Over the past 4 years, I have worked to turn these principles into action. I have voted against measures I believed did not serve students and families, and I have pushed for transparency when the easy thing to do would have been silence.
For example, I questioned and voted against the superintendent’s pay raise that was higher than nurses and custodians, pressed for more thorough investigations by the administration, and demanded transparency when others would have preferred closed-door decisions. The failure to provide a thorough investigation related to the soccer coaches was utterly unacceptable. We must do better.
I pushed early on both redistricting and reducing transportation costs, long before these issues gained traction. And while I am excited about the new Long Lots Elementary School, I have also insisted on planning for a new Coleytown and modernization of Kings Highway to ensure that all our schools are equipped for 21st-century learning.
These are not always comfortable conversations. But the role of a Board of Education is not to protect the administration; it is to advocate for students and families. That means asking hard questions, challenging assumptions, and being willing to admit when the district can and should do better.
To be clear, Westport has much to celebrate. Our teachers are talented, our students achieve at high levels, and our community provides remarkable support for education. But real strength comes from reflection, not complacency. A district that only congratulates itself is a district that risks standing still. A district that welcomes scrutiny, by contrast, is one that grows stronger over time.
Looking ahead, Westport faces major building projects, budget pressures, and transportation challenges. Each requires tough decisions, balancing ambition with fiscal responsibility. At every step, the community deserves clarity: What will projects cost, what will programs deliver, and how will changes affect families? Without transparency, these decisions risk being made in ways that erode trust. With it, they can become opportunities to strengthen that trust.
If I am given the chance to serve another term, I will continue to ask the questions that need to be asked — not to obstruct, but to ensure that decisions are made openly and responsibly. I will work to make sure investigations are thorough, budgets are clear, and major initiatives are explained honestly to the public.
Westport should expect nothing less than a Board of Education that is independent, transparent, and willing to hold itself to the highest standards. That has been my commitment over the past four years, and it will remain my commitment moving forward.
I would be honored if Westport voters would consider writing in Robert Harrington — whether by mail or on Election Day — to continue the work of putting accountability at the center of our schools.
Today, Will Enquist looks at artificial intellgence. 
To me, relying on a chatbot only adds to the pressure that can make school so stressful. Sure, AI might be able to relieve you of an especially heavy workload one evening, but in the long run the diminishment of your ability to think critically and create polished academic writing will surely catch up with you.
