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 Education is:
What are the biggest misperceptions you’ve heard about your candidacy for the Board of Education, and/or your prior service to the town?
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Democratic Party-endorsed candidate Abby Tolan (incumbent) says:
The charge that the board rubber stamps our superintendent has come up a few times in this campaign.
The truth is, any board must operate in a civil and collaborative way in order to get things done. This board has done that. We ask questions of our superintendent and our administrators, and we work together to come to decisions and, sometimes, to compromise. I am proud to have been part of that work.
Abby Tolan
The board must hire a superintendent whose vision and philosophy align with community needs, and evaluate his performance regularly. The fact is, we agree with a lot of what Superintendent Scarice does.
Some candidates may be upset by making the high school phone-free during the day. Some might not be happy with the outcome of the soccer coaches’ contract non-renewals. Others are opposed to our social and emotional learning.
My work on the Board of Education and my candidacy have not been about my personal agenda, but have been about how I can advocate for every child in the Westport schools so they can achieve and thrive.
I am a former educator. I am versed in special education, and I care deeply about the success of the whole child — academic, social, emotional and ethical.
As a Board of Education, we have important work to do. We must provide the opportunity for academic achievement to every child in a fiscally responsible way for the town. We will look at how artificial intelligence will impact teaching and learning.
We will continue to help address our children’s mental health in concert with families in a complex and changing world, and we will work with other town boards to make sure the quality of our facilities matches the quality of our education.
And, as happens every year, we must be nimble and able to pivot to address pressing issues that we couldn’t have anticipated. I would be honored to do this work on your behalf.
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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:
There are 2 big misconceptions about my candidacy: that I treat education like a business, and that I am always critical of our administration.
The first misconception likely comes from my professional background in finance and digital assets. Some people assume I see education through a corporate lens. In truth, my focus has always been on fairness, transparency, and doing what’s right for students, staff and families.
Robert Harrington
Fiscal discipline isn’t about cutting — it’s about respect: respect for the teachers and staff who make our schools great, and respect for taxpayers who expect accountability. We need to make sure that every dollar goes to the most effective areas — the classrooms, programs, and people that have the greatest impact on learning. My experience simply gives me the tools to ask tough, data-driven questions and ensure decisions are grounded in evidence and good judgment.
Over the past 4 years on the Board of Education, I’ve built a record of doing exactly that — asking hard questions, demanding clarity, and speaking up when something doesn’t sit right. That includes times when I’ve been openly critical of the superintendent and the board majority.
I voted against the 4% pay increase and early contract renewal for the superintendent — an increase higher than what was awarded to custodians and school nurses — because I strongly believed it was the wrong decision. It sent a terrible message to the employees who keep our schools running every day. This was the wrong year to make that award.
I’ve also been outspoken about the handling of the Staples soccer and tennis coach non-renewal hearings in 2025, where key process steps were missed. Unfortunately, the BOE turned its back on the former Staples soccer coaches.
It’s fair to make coaching changes — but it’s wrong to undermine the reputation of loyal, hardworking educators, employees, and community members in the process. Fairness and due process should apply to everyone.
In addition, I’ve been critical of several investigations related to the coaching situations and other serious matters, including bullying and antisemitism cases, where the process lacked consistency and where the so-called “safety plans” set up by the administration can sometimes appear to reward the bully while hurting those being bullied.
These are deeply important issues. When students and families feel that systems are protecting aggressors instead of victims, trust erodes and confidence in leadership declines. Every student deserves to feel safe, supported, and heard.
However, the second misconception — that I am always critical — is simply not true.
In most situations, I have been a strong supporter of our superintendent and administration. I’ve been one of the leading board members cheering on his forward-thinking and visionary strategic plan, and I’ve encouraged him, both publicly and privately, to take bold risks and lead with conviction.
The new cellphone ban and inclusion of AI in the district’s strategic plan are good examples of courageous policies I’ve fully supported. I also stood by him when parts of the community pushed back against the Equity Plan and social-emotional learning (SEL) in our schools.
I also backed the superintendent when he sought more resources for the facilities team, even when both Democratic and Republican board leaders would not. That kind of support doesn’t make headlines, but it reflects my belief in empowering leadership while maintaining accountability. When I see something wrong, I call it out. I won’t apologize for asking tough questions—but I also give credit where it’s due.
And finally, I’ve consistently put talent and leadership ahead of party loyalty. I’ve voted for Republicans, Democrats and unaffiliated candidates. I’m the only person in this election openly supporting both a Republican (my former running mate) and 2 unendorsed Democrats (Jodi and Stephen) alongside my own candidacy.
When my former party nominated two extreme candidates last election, I broke ranks and supported Jill Dillon, Lee Goldstein and Neil Phillips. I often disagree with Lee and Neil — but when it truly mattered, I put our school system ahead of politics. I paid a price for that decision when Republicans didn’t renominate me, but I have no regrets.
At its core, my candidacy is about integrity, independence, and putting students first. Westport deserves leaders who think critically, act fairly, and stand up for what’s right — no matter the politics.
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Republican Party-endorsed candidates Dorie Hordon (incumbent), Michelle Hopson, Andy Frankel and Kaitlin Zucaro say:
The biggest misperception about our candidacy is the suggestion that this election is about partisan politics. It is not.
The issues in this campaign are hyper-local. This is about leadership, not party affiliation, and what is best for the students and taxpayers of Westport.
Each one of us – Dorie, Andy, Michelle and Kaitlin – is an independent thinker with distinct backgrounds and perspectives. Yet we share common values: the importance of respectful civil discourse, the need to listen to parents, and the responsibility to focus on issues that matter most. We want to improve our schools, prepare our students for the future, and ensure accountability in how decisions are made.
From left: Michelle Hopson, Dorie Hordon, Kaitlin Zucaro, Andy Frankel.
Few matters are as local as the direction and operation of a town’s schools. That’s why we were surprised to see the “Harris-Shackelford BOE 2025” campaign committee’s financial disclosures showing more than $31,000 in campaign contributions.
Even more surprising—as of October 10 nearly $25,000 of these donations came from lawyers at Susman Godfrey – Mr. Shackelford’s law firm – living in Houston, Austin, Los Angeles, Beverly Hills, New York and elsewhere.
These are individuals with no apparent connection to Westport schools. All told, excluding the candidates themselves and their spouses, less than $3,000 of their $31,000 came from Westport residents.
By contrast, contributions to our campaign have come from Westport residents who share our vision for improving our schools. In this digital age, running for local office does not require extravagant spending. Our entire budget so far is about $5,000, enough to cover lawn signs, community coffees and outreach materials.
Fiscal discipline is not just a talking point; it reflects how we operate. We are also deeply grateful to the parents and residents across town who have enthusiastically volunteered their time and energy in support of our efforts.
It is worth noting that Susman Godfrey, which reported revenues of more than $528 million in 2024 and profits of nearly $1.9 million per lawyer, is the same firm that represented the soccer coaches in their dispute with the school district over the non-renewal of contracts. The coaches, now claiming lack of due process, were represented by a Harvard-educated Susman Godfrey attorney who clerked for the US Supreme Court.
Our district is now defending against a frivolous lawsuit brought by another firm, consuming time and taxpayer resources. Having played a significant role in fueling that controversy, Mr. Shackelford now claims the Board should have a “partnership” with the superintendent and “mutual respect.”
Whatever the merits of their candidacy, lawyers in Texas, California and New York should not be funding or influencing the outcome of Westport’s Board of Education election. Is this what we want our local elections to become? Our schools and our children belong to this community.
We need a board that listens, respects, and collaborates and provides direction and oversight to the administration. We need a board that restores focus on academic excellence and the issues that matter most — and can actually get things done. That is why the 4 of us are running.
Early voting has begun. Come out and vote.
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Two Democrats will be on the ballot as petitioning candidates, having secured over 400 signatures. Jodi Harris and Stephen Shackelford say:
One of the biggest misperceptions we’ve heard about our candidacy is that this race is about replacing the superintendent.
It is not. This election is about leadership at the Board of Education, and the future of Westport schools. It’s about whether the BOE can govern confidently and proactively, working with our superintendent to overcome blind spots and protect our public schools.
Stephen Shackelford and Jodi Harris.
Another major misperception has to do with “endorsed” candidates.
The Westport Democratic Town Committee endorsed 2 candidates for the Board of Education, highlighting their vetting process. In August, one of those candidates withdrew from the race. The other candidate, who is an appointee on the current board, has access to party-provided resources like funding, voter data and campaign coordination.
We did not receive the 72-member DTC endorsement, so we don’t have access to party resources. But we wouldn’t trade our route to the ballot for anything. We earned our spot by securing the handwritten, in-person signatures of more than 440 registered Westport Democrats. That grassroots effort represents real people valuing choice beyond party-appointed candidates, and it allowed us to hear directly from residents about their most pressing concerns.
This choice between party endorsements and grassroots-driven candidates is playing out across the entire race. While 5 candidates have been endorsed by official political committees (including 4 Republicans), the other 3 candidates for the BOE are challenging that system: the two of us, who petitioned our way into the race, and Robert Harrington, who is running as a write-in candidate after the Republican Town Committee shut him out. We believe Westport deserves a choice that places people over politics.
Another misperception is that protecting special education requires direct personal SpEd experience. While one of us has unique personal experience, the real issue is systemic. We’ve heard from many families about their enormous, costly challenges securing the services their children need.
Though some experiences are positive, this uneven access to support has festered for years. The board needs independent voices willing to challenge this status quo and its high costs to both families and taxpayers. We will be those voices.
This brings us back to the larger misperception: that this race is about one person, one event, or one group of stakeholders. It is not.
It is about whether the BOE has the strength, skills and independence to set direction, manage risk, and provide effective oversight. When boards lose confidence in their own role, they invite chaos. When they fail to lead, they leave the administration and community vulnerable to missteps.
Healthy debate is not dysfunction; it’s how good governance works. The real danger comes when boards avoid deliberation, shy away from transparency, or operate without clear priorities.
That vacuum leads to confusion and unnecessary conflict. It also creates an opening for louder, more ideological voices to dominate the conversation — voices that want to bring national culture wars into local classrooms, question professional educators, and erode support for public education itself.
Between us, we bring deep experience in law, communications, negotiation, strategic planning and community leadership. We are not running to dismantle the system, but to strengthen it — by restoring accountability, elevating standards of leadership, and ensuring decisions are made transparently.
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For last week’s “Where We Stand” story, click here.
For the second “Where We Stand” story, click here.
For the first “Where we Stand” story, click here.
