Editor’s note: Following is an opinion submitted by Westport resident and Board of Finance candidate Brian Gaines.
I’ve appreciated the active debate in our town media about the race for Westport First and Second Selectman. With all three candidates either registered Democrats or Independents who share mostly similar positions, this race is not about ideology — it’s about experience and proven leadership.
In my view, one candidate stands out: Don O’Day. Don has a long track record of making tough decisions and engaging in town government as chairman of the Board of Education, RTM member and chairperson of multiple critical and complex school building committees. His running mate, Andrea Moore, brings her own direct experience as the current Second Selectwoman and past experience on the Board of Finance. Together, they’ve already shown the aptitude to navigate complex town issues.
Of course, real leadership means making real decisions. That sometimes leaves people disappointed as no one can satisfy every interest group. But in Westport, most residents understand that decisions, such as relocating the community gardens while managing the Long Lots building committee, involve balancing many voices and priorities. Don did that thoughtfully. He also managed the Coleytown Middle School project with transparency and efficiency, pushing for a remodel that saved money and avoided years of overcrowding.
By contrast, candidates with little experience have never had to make hard decisions and can present themselves as all things to all people — nodding along with every concern while avoiding accountability. For example, as an RTM member, one opponent now claims he should have spoken out more on the community gardens issue while still not expressing a clear opinion on what he would have done. Similarly, when asked to take a position on the Superintendent’s non-renewal of a soccer coach, the other candidate abstained. That may avoid controversy, but it isn’t leadership and certainly seems like an obvious attempt to pander to all voters.
Don, on the other hand, has done the work. He has faced real issues, weighed all sides, and put in the effort to reach decisions in the best interest of the town. You won’t find anyone who questions his understanding of the facts or his commitment to Westport.
When people call for a “fresh start,” I wonder what town they are looking at. Westport is already a well-run, collaborative, and thriving community. During COVID, Don helped lead the rebuilding of Coleytown Middle School with remarkable efficiency. He also guided the successful funding of a new elementary school. These are real results and not just platitudes.
We’re fortunate to have three good people running, but in this race, only one candidate slate brings proven experience, clear accomplishments, and demonstrated leadership: Don O’Day and Andrea Moore.
Brian Gaines
There are really only two things you need to think about when you consider the O’Day-Moore ticket.
First, they are offering “four more years” of the incompetence of the Tooker-Moore administration. Whether it was the Downtown Parking planning debacles, the threats to Jesup Green, the destruction of the award winning Westport Community Gardens, the Tooker-Moore administration made insular decisions and ignored the general public. Yes, we can expect Don O’Day to ignore the general public, just as he did on the LLSBC.
Can Andrea Moore explain why the Tooker-Moore administration ignored requests from CT DOT for feedback on the site of their maintenance facility? The utter… incompetence? laziness? of the Administration to not reply to the State, nor seek feedback of the neighbors regarding this simple request led to clear-cutting of land and harming of the property values and quality of life of residential neighbors. I don’t imagine anyone wants four more years of that.
Additionally, looking at the national leadership of the GOP, it is a political party attacking press freedom, attacking academic independence, deporting people without due process, and putting our Constitutional norms under threat. In the wake of all of that, many people of character have left the Republican Party. What did Don O’Day do? He joined them! He found his people. I can’t imagine being that desperate to want that job. Are these the values that Westporters expect from their leaders? Is this moral leadership? The obvious answer to both of these questions is a resounding “no.”
We have two far more appropriate candidates for the job. Personally, I’m voting for David Rosenwaks, who is campaigning on a platform of transparency in our Town government. But Westport can do better that four more years of Tooker-O’Day-Moore.
Chis summarizes quite well exactly why Westport’s residents should NOT vote for Mr. O’Day and Ms. Moore. Enough is enough.
The stench of 4 years of divisiveness, vitriol and petulant that our residents witnessed under Moore’s and O’Day’s non-transparent “leadership” under Ms. Tooker’s thumb still permeates the air.
The O’Day/Moore slogan “Experience Matters” is absolutely correct – just not in the manner they intend. The experience (as Mr. Grimm briefly reminds us) that Westport’s RESIDENTS were forced to endure matters, and should never again be given a home in Westport.
We do not want or deserve to relive that shameful experience.
I have respect for Brian Gaines and believe he would be a thoughtful addition to the Board of Finance. Unfortunately, his recent message does not tell the full story.
Portraying Mr. O’Day as a “leader” who makes tough decisions misrepresents his record. Leadership is not reactive; it is proactive and visionary. True leaders anticipate challenges, unite people around solutions, and implement plans that prevent crises before they arise.
Mr. O’Day’s record reflects the opposite. As Chair of the Coleytown Middle School Building Committee and a member of the Long Lots Building Committee, he played key roles in projects that were themselves the result of earlier inaction. The more telling moment came during his tenure as Chairman of the Board of Education, when he could have championed a comprehensive environmental survey of Westport’s school infrastructure—an initiative that might have identified structural and environmental risks early and guided a long-term, cost-effective maintenance plan.
Instead, he deferred to an overbearing superintendent.
The consequences are clear: $32 million to restore Coleytown and $103 million to rebuild Long Lots. While not every issue could have been avoided, decisive, forward-looking leadership could have reduced costs, disruption, and the need for crisis-driven decisions.
Westport deserves leadership that looks ahead—leadership with the foresight and courage to act before problems escalate.
Vote for leadership with vision and conviction.
Brian,
I agree 100% with your endorsement of Don O’Day and Andrea Moore for First and Second Selectman of Westport. It is sad so many continue to bash and spread false information about these two dedicated Westport public servants. Don and Andrea are proven leaders who have always stepped up for the best interests of our town, residents, and children.
One should first “participate” in our local democracy before thinking they can lead. Leadership will always come with criticism, as leaders have to participate in an arena where you can’t please everyone. Democracy is not easy.
When Coleytown Middle School was in crisis during Covid, Don O’Day was asked to step up, and he delivered. On time and under budget, a newly refurbished Coleytown Middle School. Updates during construction were daily and “transparent.”
The Long Lots Building Committee, which Don O’Day has been a member, and huge contributor, stepped up again. There were over 55 meetings, all noticed and transparent. Don spoke up and stood up for our kids, parents of both Long Lots and Stepping Stones to get this much needed school moving forward.
Voters do your homework, ask questions. Leadership and results don’t come from all coffee’s at local cafe’s. Leadership comes with experience, participation, and yes some criticism.
Jimmy Izzo
RTM 3
And yet, on the first day of the first phase of Long Lots construction, nobody from the LLSBC was to be seen, when site plans were disregarded and areas designed to be buffer for the neighbors were cleared. (See today’s 06880 coverage.) I guess Don was too busy campaigning.
Exactly this, Chris. It is disingenuous of Don to to pretend to care and actual espouse fairness and transparency after the backstabbing/villifying that took place against members of the Community Gardens to get their way for the Long Lots school committee. That alone is enough to cast your vote for ANYONE ELSE than those who seek to continue the policies and actions of the current administration.
A “fresh start” might entail honesty, following through on promises, and making sure that agreements are adhered to.
Why O’Day/Moore have already failed on Day One of the Long Lots school replacement is easily understood if one sees their candidacy as a continuation of the present administration: no accountability, no integrity, no care or concern for residents in the path of hasty, ill-thought out and irresponsible plans.
It seems to have happened again and again with everything touched by the current Republican administration: the Gardeners, Longshore, Longlots School, Downtown parking, the Hamlet, CTDOT’s garage, the Cribari Bridge…
An election seems to be the only thing that might stop this juggernaut of compounding disastrous decisions.