CT Patch Candidate Profile: Stephen Shackelford For Board Of Education

WESTPORT, CT — The 2025 election is heating up in Connecticut and there are plenty of races with candidates eager to serve in elected office.

Connecticut Patch asked local candidates to answer questions about their campaigns and will be publishing candidate profiles as election day draws near.

Candidate's Name:
Stephen Shackelford

What office are you seeking?
Board of Education

What town do you live in?
Westport, CT

Campaign Website
https://harrisshackelford25.com

Party Affiliation:
Democrat

Occupation:
Trial lawyer (20 years) at Susman Godfrey LLP

Family:
My amazing wife Stefanie is likely known to many voters, as she has been deeply involved in PTA leadership for years. We have four kids: two graduates of Staples who are currently juniors in college; one at Staples currently; and one at Coleytown Middle School, who will be at Staples next year.

Does anyone in your family work in politics or government?
No

Previous public office, appointive or elective:
Yes. I served on the Westport RTM (District 8) for four years, 2019-2023.

Why are you seeking this office?
Our BOE needs new voices and real change. For some reason, it's taking years to fix small problems, which become big and more expensive problems, particularly when it comes to school facilities. Our teachers face staffing shortages (paraprofessionals and substitute teachers) that make it harder to do their jobs. Our special-education program, while working well for some, forces far too many families to seek expensive outside help to get the resources they need. And these problems persist. Yet in one meeting after another, a majority on the BOE is doing less and less to engage our superintendent in meaningful debate about what needs to improve, or ask hard questions about the proposals he brings to the Board. Community members, and sometimes one or two voices on the BOE, raise issues or concerns, but the majority fails to engage.

I'm running with Jodi Harris to put a critical mass of independent voices onto the Board, who will bring responsiveness, transparency, and good governance back to the BOE.

The single most pressing issue facing my constituents is ____, and this is what I intend to do about it:
Leadership on the BOE. There are plenty of specific challenges facing our school district — I get to those in a later question — but the most pressing overarching issue with our Board today is a failure of leadership. Some on the current Board believe its job is to hire the best superintendent of schools possible, and then get out of the way. My running mate, Jodi Harris, and I disagree.

The superintendent's role is multifaceted and critical. He has numerous managerial responsibilities, but he also should be the district's visionary leader, challenge assumptions, and propose bold initiatives to move our schools forward. The Board's role, as the elected voice of our community, is to ensure that vision is thoroughly vetted, financially sound, and easily measured for maximum impact.

Effective oversight by the Board is not passive agreement, but far too often lately, that's what we've seen out of the Board majority. Too many board meetings have featured major proposals approved with minimal questioning from the majority, despite valid concerns raised by the community and even other board members. That is not healthy governance; it fails our students, our educators, and ultimately our superintendent.

Rigorous oversight is not about micromanagement; it is about foresight. It's about asking the hard questions, and insisting on actual answers before moving forward, so as a community we can achieve the best outcomes and avoid negative consequences. 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.

A well-functioning BOE also brings to light issues the administration may have missed, or not properly prioritized, including issues raised by Westport voters and other stakeholders that the administration has failed to address. We're all human; everyone has blind spots. We have a governance structure with a superintendent and a BOE that is meant to account for that, and that's yet another reason it's important to have BOE members like Jodi Harris and me who are committed to a proactive, engaged, responsive Board.

What are the major differences between you and the other candidates seeking this post?
Only one of the eight candidates for BOE this election, Abby Tolan, supports how the current Board is operating; the other seven candidates — including my running mate, Jodi Harris, and I — believe it’s time for new voices and real change in how the Board operates. Ms. Tolan is a dedicated public servant, no doubt, but she is firmly ensconced in the current Board majority that has fallen well short of where our Board should be when it comes to governance, oversight, responsiveness to the community, and transparency.

The two other incumbent BOE members running for re-election, Dorie Hordon and Robert Harrington, have shown considerably more independence during their time on the Board. I respect that, even though I certainly don’t always agree with them. I have been disappointed recently, however, in false and ill-considered attacks coming at me from the official Republican slate, which includes Ms. Hordon but not Mr. Harrington (whom the town Republican party refused to endorse).

As for the other three candidates, all members of the official Republican slate, I just don’t know much about them. And I haven’t been able to decipher much from their campaign literature, other than that they seem to be unhappy with aspects of the school curriculum. If that’s a foundational part of their campaign, then that is certainly a difference between us. Although I’m always happy to discuss areas of potential improvement with any stakeholders, including improvement in curriculum, I am wary of anyone running for BOE in hopes of engaging in large-scale curriculum overhaul in our school district. That’s something I don’t think is needed, and is best left up to educators, in any event.

What other issues do you intend to address during your campaign?
There are many issues facing our district right now. To name a few:

FACILITIES: The full replacement of Long Lots Elementary is the beginning, not the end, of the work we must do to repair school facilities that have been neglected for too long. Coleytown Elementary has needed serious attention for years, from top to bottom. The Staples auditorium hasn’t been touched in more than 30 years. There is no working girls’ locker room at Staples; girls’ teams change in hallway bathrooms and classrooms. Kings Highway Elementary has a basement gymnasium and cafeteria that don’t meet ADA requirements.

Despite all these serious issues, the Board has failed to move with the necessary urgency. For instance, the Staples auditorium was offline for over a month this past spring when rigging equipment failed and was stuck on the stage, forcing the relocation of numerous events and performances. Yet the Board has had reports from outside firms calling out the rigging problems since 2022. Over the last several weeks, the Board has finally started to move forward on some of these projects. That’s great, but we need a Board that focuses on fixing these problems year-round, not just at campaign season.

My running mate, Jodi Harris, and I will push for a comprehensive budget for completing all major needed projects over the next several years, so we can make informed decisions about different options for fixing problems, and intelligently prioritize and allocate spending, including necessary trade-offs. We also will push the Board and the First Selectman’s office to embrace public-private partnerships to fund major capital projects, tapping alumni, current families, and local businesses to fund major projects (as other local school districts do).

SPECIAL EDUCATION: There’s a serious lack of continuity and quality in special-education services, especially as students transition from elementary to middle schools. We’ve heard countless stories of families that have had to spend large amounts on private advocates and even lawyers to get the services their children are entitled to — services that were game-changers when they finally were provided. Jodi and I propose creating a new position of special-education ombudsman, who would ensure families are heard — without fear of retaliation — saving many families from having to hire outside advocates and lawyers, and reducing the number of legal issues and costs for the district. We also will push to bolster resources for Intensive Resource students.

TEACHERS, ADMINISTRATORS, AND STAFFERS: Many elementary-school teachers are desperate for help, especially more paraprofessional support. At the middle-school level, a lack of substitutes means teachers lose their prep periods to cover the classes of their colleagues. For these and other staffing shortages, finding ways (like public-private partnerships) to fund major capital projects outside of our annual budget will help us pay for solutions. But many of these issues aren’t being raised in any meaningful way to the BOE. Jodi and I believe the BOE should do much more to ensure the administration eliminates obstacles that get in the way of teachers teaching. It should prioritize meetings to hear the obstacles and debate creative solutions, policy changes, and budget priorities to tackle these issues.

LEGAL: Finally, as I discuss in the next section, we face many other potential headwinds as a school district in the coming years that may come down to legal challenges, and I think I’m uniquely well situated to help the district navigate such challenges, given my professional background.

What accomplishments in your past would you cite as evidence you can handle this job?
I’ve been a trial lawyer for 20 years, which means I’ve been trained to analyze problems with a determined attention to detail, and to think creatively when an obvious solution doesn’t present itself. I’m proud to have taken on some of the most challenging cases against some of the most powerful people and organizations around, including representing Dominion Voting Systems in its landmark litigation against Fox News, and currently representing the American Bar Association in its constitutional challenge to the current Administration’s policy of using executive orders to try to intimidate major law firms. I’m proud that when my firm, Susman Godfrey, was targeted with one of those executive orders, we did not hesitate to challenge the order in court, and thus stand up for ourselves, our clients, and our profession. I will bring that same determination and commitment to doing what is right to the Westport BOE.

My specific legal expertise will also be useful to the Board as we face potential challenges from the current Administration, which is focusing on attacking “blue states” like Connecticut, and has a particular interest in trying to influence education policy.

I also served four years on the Westport RTM, from 2019 to 2023. If you want to know how I’ll work with colleagues on the BOE, I encourage you to talk to anyone I served with on the RTM. I think you’ll hear I was a thoughtful, engaged RTM member who collaborated respectfully with other members of all sorts of viewpoints and political backgrounds, to achieve progress together for our town.

What is the best advice anyone ever gave you?
That’s a hard question, as I have been blessed with lots of good advice over the years!

Among the best advice I’ve ever received is, never be afraid to admit when you got something wrong. We learn the most from our failures and mistakes, and a willingness to change course when confronted with new facts is not weakness. We are at our best when we remember that nobody has a monopoly on wisdom or the truth. That doesn’t mean act like a weathervane! But it does mean always approach debates and discussions with an open mind. When we have seven Board members willing to do that, we’ll have an incredibly effective and powerful BOE.

Is there anything else you would like voters to know about yourself and your positions?
I’m always happy to answer questions or discuss issues with voters, just reach out to me and Jodi at harris.shackelford@gmail.com.

I do think it’s worth briefly explaining how the race for BOE is working this year. Our BOE has seven members. Four of those spots are up for election this year; the other three will be up in two years. There are eight candidates running. Three of those candidates are Democrats, and will appear on the Democratic line: me, Jodi, and Abby Tolan (the only incumbent Democrat running for re-election). Four of the candidates running are Republicans (including one incumbent, Dorie Hordon), and one (Robert Harrington, also an incumbent) is independent, running as a write-in candidate.

Voters can choose up to four people to vote for, but aren’t required to use all four of their votes. Under Connecticut state law, each political party is limited to no more than a bare majority of any local board, including the BOE. There are already two Democrats on our BOE who are not up for re-election until 2027. That means that only two of the three Democrats running in this election this fall can be seated on the Board. In other words, even if Jodi, Abby and I were to finish in the top three in terms of vote totals, only two of us would actually win office (the top two vote-getters out of the three of us).

If that's confusing, feel free to reach out to our campaign to answer any questions.