Editor’s note: following are opinions submitted by Westporters Eugene Shapiro and Jay Keenan.
O’Day/Moore are the clear choice for selectmen
As a lifelong Democrat, I have followed this year’s First Selectman race closely. I watched last week’s Y’s men debate with an open mind, but it quickly became very clear to me that Don O’Day and Andrea Moore are the clear choice to lead our town. They are the only candidates with both corporate and government experience, financial expertise, and a proven track record of accomplishments.
Among his many career accomplishments, Don was a Chief Financial Officer at Citi. He has successfully led teams, managed budgets, and planned and implemented complex projects. Andrea has 20 years of experience on Wall Street. If our town faces another crisis like COVID, a financial downturn, or a weather emergency, we need a leader who can make decisions, manage teams of employees, and maintain our finances. In times when strong, steady leadership is needed, we can trust Don and Andrea to make tough choices and advocate for the best interests of our residents.
In addition to decades of corporate work, Don has served as Chair of the Board of Education, Chair of the Coleytown Middle School Building Committee, an RTM member for his district, and as a member of the LLS Building Committee. Don managed the Coleytown Middle School crisis and completed the renovation on time and on budget, even during delays and cost pressures at the height of Covid. Andrea has served as Second Selectwoman, Vice Chair of the Board of Finance, an RTM member, and as an active volunteer in the schools and preschools, including President of the Board of Directors of A Child’s Place and President of the Saugatuck Elementary School PTA. Andrea and Don have lived in Westport for decades and understand how to achieve results locally and within the state.
Don and Andrea are the experienced and skilled team we need to lead Westport for the next four years. Please join me in voting for them on Tuesday.
Eugene Shapiro
Lansdowne
Westport
O’Day Moore Endorsement
Perspective
Having been intimately involved in Westport’s government for more than 20 years, I bring a perspective few others can. I have served on the RTM for two decades, where I currently chair the Public Works Committee and serve on the Planning & Zoning, Employee Compensation, and Ethics Committees. Beyond the RTM, I’ve been a Trustee at Earthplace and have contributed to several major town building committees; including Bedford Middle School, Staples High School, Kings Highway Elementary, and Coleytown Middle School. I currently chair the Long Lots School Building Committee.
Through these roles, I have worked closely with each of the current candidates, as well as every level of town government and the last several First Selectmen. This experience gives me a unique and informed perspective on the abilities on what it takes to serve effectively as First Selectman. Having worked with Andrea in her roles on the RTM, Board of Finance and Board of Selectman and Don on the Board of Education, RTM, and multiple School Building Committees, I can without hesitation endorse them wholeheartedly as our next First and Second Selectpersons.
Democrat or Republican
While I fully understand that some may feel strongly about party affiliation and I fully respect that, these labels have little bearing when it comes to managing the business of the Town of Westport. Neither the Democratic nor Republican candidates are beholden to anyone but their family and the Town of Westport as claimed by one candidate.
We should all be excited about Don O’Day’s candidacy, not simply because he is a good friend, but because he is the most qualified candidate to manage Westport’s affairs. Don is a lifelong Democrat who has earned the endorsement of the Republican Town Committee. That alone should be national news. It’s an example of what local government should be; looking beyond partisanship to support the most capable leaders.
Rather than endorsing along party lines, the RTC recognized that national politics have no place in Westport’s local governance. They focused instead on who can best serve the Town; and that’s Don.
Westport is all good
At the last debate, I was disappointed to hear one candidate describe Westport as “mired in partisan politics” and “in need of fixing.” Westport is not broken. Of course, there are always things we can do better, but this is already a great Town, an extraordinary place to live and raise your children. We have good, caring, smart people, excellent schools, a vibrant downtown, wonderful restaurants and shops and, of course, Compo Beach and Longshore. Why is Westport so great? Because of people like Don O’Day, Andrea Moore and the countless volunteers who have selflessly devoted their time and energy to keep Westport the Town we all love to call home. That hasn’t changed in my 28 years of living here.
The job
The first selectperson’s position is not ceremonial; it is a full-time management job. The ribbon cuttings and photo-ops are but a tiny fraction of the job. You are the CEO and COO of the Town of Westport. There are 17 different departments all directly reporting to you and every day you have to make decisions on budgets, which construction projects to prioritize (bridges, roadways, culverts, golf course, marina) set up committees, employee hiring, union contract negotiations, solid-waste contract negotiations, vendor contracts and prioritization of the $431 million in the 10-year capital forecast, just to name a few. This is not a “figurehead” role, you can’t sit back and avoid hard choices. The job demands decisive leadership, not endless discussion.
This is a full contact job. The First Selectman must be willing to take a stand, make difficult decisions, and act when others hesitate.
Why am I voting for Don and Andrea
Andrea Moore, is a Westport native who grew up on Partrick Road, graduated from Staples High School and, since returning to Westport to raise her three daughters, has spent more than a decade working to preserve and enhance Westport through roles on school boards, town committees, and the Board of Finance, where she served as vice chair, as well as the RTM. As our current Second Selectwoman, she is the only candidate with direct experience in the role. She has personally vetted over 100 candidates for placement on Town committees and fully understands the daily management responsibilities of the office and will be instrumental in facilitating a smooth transition. No learning curves, no need for listening tours to understand how departments operate; she is also a genuinely nice person.
Don is a 31-year Westport Resident; he and his wife Toni raised three children who all attended the Westport schools. Don recently retired from a 40-year career in finance, culminating as the CFO of Citi’s Home Equity Business. He was elected twice as a member of the Board of Education (BOE) and served as Chairman for four years and currently serves as a member of the RTM.
As BOE chair he reformed the school budget process, raised graduation standards, improved transparency in the special education process and, under his watch, Staples High School was named the #1 high school in CT for the first time. On the RTM, Don is on the Public Works and Finance Committees, arguably the most demanding committees on the RTM.
Don also chaired the Coleytown Middle School Building Committee (CMS). As a member of the CMS committee, I saw first-hand how much time and effort was put into that project by Don O’Day. A project which finished on-time and under budget during a pandemic and saved the town $40 million dollars by supporting renovation over new construction. Don was commended for both his tireless efforts on behalf of the CMS community but also his transparency during the entire project, and was even nominated as 06880’s unsung hero for his efforts. That same time, dedication and ability to make tough decisions will be brought to the selectman’s office.
Don now serves on the Long Lots School Building Committee where his financial modeling and cost benchmarking was instrumental in the Board of Finance’s unanimous approval of the project. Don also championed geothermal heating and cooling and PV technology to advance the first ever sustainable building in Westport’s history.
Don and Andrea will hit the ground running on day one.
A note to the Long Lots community
When you go to the polls on November 4th, remember this; after three years of volunteering to rebuild Coleytown Middle School, after retiring from a 40-year career in finance, and with no children left in the school system, Don O’Day was still the first to step up to join the Long Lots School Building Committee. When your voices risked being drowned out, Don spoke up when others remained silent and for the past three years, he has tirelessly brought steady leadership and unwavering resolve, volunteering his time and speaking up on your behalf to get Long Lots and Stepping Stones approved and built. As he always likes to say, “it’s about the kids” …your kids. Don and Andrea are the right people to protect and strengthen our remarkable Westport Schools…CES is next.
It’s hard to argue with the record of selfless volunteerism and vast experience that the O’Day Moore ticket represents.
I hope you will join me in voting for Don and Andrea on November 4th.
Jay Keenan
Chair, Public Works Committee
RTM District 2 Member (2005-present)
Chair, Long Lots School Building Committee




Ya ! I don’t think so. And I am a Westport resident 23 years.
I am a mom of 4, multiple business owner, and as far as I see this, for businesses in town, is a disastrous ticket.
They weren’t even smart or savvy enough to put their outrageous collective arrogance aside and even “pretend” to care about businesses.
It’s laughable and scary that these 2 jokers might have a shot at being our elected representatives, running our town.
Neither has ever owned a downtown business and nor have they the first clue, what these businesses need.
If they did they would have met with us as we requested.
But no.. they have a multi year absolutely failed agenda they are hoping to bully through the PZ, which promises to destroy businesses in town.
Again.. longevity in town does not mean having a singular clue about running retail/restaurants.
If either one of them had opened a downtown business it would have been bankrupt within a year.
They are both a liability for our downtown, huge liability.
Ask 99% of merchants.
We are all in agreement.
Ask the gardeners… ask any number of groups in town this posse sees as special interest.
Ya.. no way they will be good for our town.
I see gargantuan law suites and having to adopt a zero tolerance to the bully boy pulpit of these 2 clowns.
Nepotism, and bullshit is what this ticket brings.
As a huge investor of my personal money in businesses in this town, I can tell you these 2 will ruin the downtown. It is their intention.
Other than helping out the likes of the inn at Longshore and profligately pissing away your hard earned and paid property taxes on ostentatious and irresponsible agendas, this ticket, is a disaster.
Civic engagement is healthy, but the vitriol in this comment is unbecoming and does not align with the kind of respectful discourse that Westport deserves. We can and should debate ideas and priorities passionately, but personal attacks and name-calling only diminish the discussion. Our town is stronger when we focus on facts, listen to one another, and work together to find common ground.
Don WAS NOT CFO OF CITI! Here we go again getting loose with the facts. He was cfo of a subsidiary to a subsidiary of Citi. That’s a big difference. He never made it to the C-Suite if Citi. In fact, one should check the record as to when he oversaw the financials of the home lending equity market because this sector can see a market and economic meltdown in the mid to late 90s after a decade of malfeasance on the part of lenders.
As for Keenan’s 1300 word epistles of Don, yes national politics does matter today. Local government is the foundation upon which rests state and federal government.
I find it cute that all these DOD supporters keep trying to draw a line between him and his party. Why is that?
Because they know that voters can see through it, and that the GOP popularity numbers are the lowest ever. They throw Garsby parties while good support for the hungry IN WESTPORT are being cut off.
You can fool some of the people, Jay…
***food support for the hungry***
Westport deserves thoughtful, fact-based dialogue that focuses on local issues, not partisan smears or attempts to tear people down. We can disagree without being disagreeable.
Great Gene and Jay. I couldn’t agree more with you both, and your endorsement of Don O’ Day and Andrea Moore as our next First and Second Selectman.
Proven Experienced Leadership!
Jimmy Izzo
RTM 3
Chair RTM Public Protection Committee