As Washington becomes more polarized, Westport’s Republicans hope to reverse that trend.
The party’s nominating committee has endorsed Don O’Day for first selectman.
That’s a historic choice for Westport — and might make national news.
The former Board of Education chair was a lifelong Democrat. Six weeks ago, he switched his registration to “unaffiliated.”
The nominating committee also endorsed Republican 2nd Selectwoman Andrea Moore, for a second term.
Theofficial selection of O’Day and Moore — tomorrow (Tuesday) at 8 p.m., in Town Hall Room 307/309 — seems assured. Though nominations may be made from the floor, no other Westporter has indicated a desire to run.
Andrea Moore and Don O’Day.
The Democrats meet tomorrow too (7:30 p.m., Town Hall auditorium). They are expected to endorse Board of Education member Kevin Christie for first selectman, and Planning & Zoning Commission member Amy Wistreich as his running mate.
O’Day’s candidacy is rooted in both “bipartisanship and non-partisanship,” he told “06880.”
It won’t be his first time seeking that kind of consensus. When he became Board of Ed chair in 2008, he bucked tradition by insisting that the vice chair come not from his own Democratic party, but from the GOP.
That vice chair, Jim Marpe, later served 2 terms as first selectman.
The Board of Finance then adopted the 2-party model for chair and vice chair. They and the BOE continue the practice today.
“I’m very, very proud of that,” O’Day says. “We built a culture of cooperation and respect that worked.
“I have a non-partisan point of view. I think the best way to govern here is in a bi-partisan way.” He is currently a member of Westport’s non-partisan Representative Town Meeting (RTM), from District 3.
The role of parties in Westport, he says, is to present candidates who support their vision of how the town should be run.
“The difference between Democrats and Republicans should be de minimis in Westport,” he says. “Nationally, I know it’s different.
“Local government should be about neighbors and solutions – not ideology. What matters most is what’s best for Westport residents, not a particular party.”
This is not O’Day’s first time in the first selectman’s race. He vied for the Democratic endorsement in 2021. It went instead to State Representative Jonathan Steinberg.
O’Day understood. He had supported Marpe’s 2 successful selectman campaigns, raising charges from Democrats of “apostasy.”
“I guess I was like Joe Lieberman,” he notes. “I chose to support the person I thought was most qualified.”
When several Westporters suggested he enter the race this year, O’Day listened. However, independent candidates are not assured a line on the ballot. He realized his clearest path would be endorsement by the GOP.
In conversations with Republican Town Committee members, O’Day emphasized his experience chairing both the Board of Ed and the Coleytown Middle School Building Committee, after its sudden closure due to mold.
The RTC was “confident I have the best interests of Westport at the forefront,” O’Day says. “This is about the town, neighbors, people — not party.
“In every meeting, I made it perfectly clear that the last Republican presidential candidate I voted for was Ronald Reagan, in 1984,” O’Day says.
“I am not close to being a Trump supporter. I’m a Westport supporter.”
Not once, he says, did the RTC “back away.”
“We may not align on all national issues,” O’Day says. “But we agree that Westport deserves pragmatic, non-partisan leadership focused on getting things done.”
He advocates “action, transparency and inclusivity — not delays or endless studies.”
His priorities include modernizing town and school infrastructure, with a focus on fiscal responsibility and sustainability; preserving Westport’s AAA bond rating through disciplined financial management; respecting local zoning while responsibly expanding affordable housing; enhancing parks, beaches and recreational facilities; and improving traffic management with an emphasis on pedestrian and cyclist safety.
“People won’t always agree with every decision,” the candidate notes. “But they’ll always understand how and why it was made. The first selectman’s office will be clear, candid and responsive.”
O’Day moved to Westport in 1994, from Long Island. “I was so proud to be here,” he says. “I’ve never lost that pride of saying I live here.”
O’Day is retired. He spent 40 years in financial services, including 35 years at Citigroup. His roles there included chief financial officer of Citi Home Equity, and chief administrative officer of CitiMortgage.
His wife has taught preschool at St. Paul’s for many years. All 3 children went through the Westport school system.
Donny, now 40, moves back in August. His 2 children will eventually attend Coleytown Middle School — and see their grandfather’s name on a building committee plaque.
“I want the same rewards for them here that my kids had,” O’Day says.
Don O’Day chaired the Coleytown Middle School Building Committee. Just before its reopening in January 2021, he posed in the renovated cafeteria. (Photo/Dan Woog)
He is excited to share a ticket with Moore. The Staples High School graduate, former Board of Finance vice chair and financial services professional offers “deep knowledge of town operations and financial control,” he says.
She shares his enthusiasm. The 2nd selectwoman got to know O’Day during his work on the CMS renovation, and cites his “even temperament and ability to get stuff done, during a really tough time.
“I was impressed by his grasp of the big picture, and his ability to bring people together for a common cause.
“At the end of the day, first selectman is a management job,” she adds. “You have 17 direct reports, a budget and so much more. Most people see the meetings and events, but the job is really running the town. Don has a great ability to do that. I hope I get the opportunity to keep doing what I’ve done, to support that.”
Washington venom will not be part of Westport’s first selectman’s race — and not just because O’Day is an unaffiliated voter.
Kevin Christie
Of Christie — the favorite for the Democratic nomination — O’Day says, “You can’t find a nicer guy. I like him a lot.
“As the Board of Education representative to the Long Lots School Building Committee, which I serve on, he asks lots of thoughtful questions.”
The difference between them? “I think I have more experience, both in town and management.”
Tomorrow night, both parties determine their selectperson slates. In November, voters get the final say.
Lifelong Democrat here
Don is one superb candidate
This is great news for Westport! Don O’Day has the personal, professional and political leadership experience and the demonstrated results that will make him a terrific First Selectman. Teaming with Andrea Moore will create a non-partisan governance approach that so many Westporters understand and appreciate. Thank you Don and Andrea for (again) stepping forward.
Don O’Day is a brilliant choice for Westport. His experience speaks for itself. The man that did more than anyone to get CMS back on its feet as Chair of the CMS Building Committee. The combination of Don and Andrea will be a real win for Westport. This is truly Westport over party.
Robert did you like how the whole long lots process was handled including the garden death, no new garden planned ever, not on the 8-24, but the fields were olannned as a senior citizen himself, he completely neglected to take care of this part of our demographic, our seniors.
Don has a long track record of success in leading our town’s initiatives. His non-partisan approach is what we need now!
If you watched the LLSBC ride roughshod over the Community Gardeners or the BOE soccer coach hearings demonstrate utter disregard for inclusion and due process, you will have seen a preview of what an O’Day or Christie administration will tolerate and defend, and it ain’t pretty.
Yes, Anytime he was questioned he seemed annoyed and angry, is that his style I wonder.
Yes, an annoyed and angry demeanor when ones absolute authority is questioned is a prerequisite to “serving” the citizens of Westport for a long time.
Don was pretty pissed off when he had to listen to petitioners ask that their town-charter granted rights be observed by the the RTM. Of course, he followed through with decisive action, along with Jimmy and Andrew and David, etc. by taking away citizens long established rights to petition the RTM.
Our rights are being eroded right here in Westport by a group of long “serving” volunteers who think they get to decide what happens in Westport.
I wish these people woudl all get a hobby, or just stick to the Rotary Club where they could at least raise some money for a good cause.
He’s an authoritarian, and a cranky guy. A massive bully. If Tooker had a twin brother, he would be it.
Giving him any kind of an opportunity to lead the town is a NIGHTMARE in the making.
4 more years of the same ole 💩.
Tooker will go down in history as likely the worst selectman this town has ever seen.
O’Day, and Moore, were there every step of the way to support her.
And their records speak 1000% to that.
As for transparency, please.
These 2 do not know the meaning of the word.
The fact that they even have the balls to use the word transparency, is in of itself an insult to those of us who have borne witness to the past 4 years.
What a joke.
More manipulation by Don 16% O’Day.
When is a Democrat not a Democrat? When he shows up on the GOP ticket. This ticket is as Red as the day is long, no matter the dissonance O’Day tries to create about nonpartisanship.
But let me measure my emotions about this first and foremost: I have a lot of respect for many members of the Westport Republicans. Likewise, there are Dems with whom I have lost confidence. I believe voters are smart enough to choose wisely.
At the end of the day, though, elections are political. The party system employed to choose a candidate is about ideology and money. The Westport GOP ticket is designed to dilute and divide Democrats. Don’t fall for it.
O’Day, you are on the GOP party ticket and that’s a fact. You say you are unaffiliated, but that won’t fill your war chest. This nonpartisan babble is insulting to both parties, and to citizens of Westport.
You come out of the gate with apologies for your decision. You are manipulating party politics to serve your own political ambition. This is not about Westport, it’s about Don O’Day.
Here’s your campaign slogan material:
—The 4% tax increase for that Big Beautiful School.
—The destruction of an award winning community garden and the exploitation of both gardeners and student body to get more ball fields.
—The decision to “intensify use”among a quiet, flood-prone residential neighborhood to build a new school while the other remains in place, and install two monstrous, lighted and probably plastic sports fields.
—The dishonest cloak-and-dagger committee work designed to subvert citizen interests.
—The frail attempts to keep important public information and deliberations behind closed doors.
All politics is local. Just say no to any GOP effort to take over every facet of our Democracy for the few, the privileged, the developers, the homogenous 1%.
No.
Being an independent most of my life, I have supported individuals vs. a party. I have known the O’Day family for many years & know Don to support what he believes is best for our town. Public service is not easy & the old saying “you can please some of the people some of the time but you can’t please all the people all the time” is pretty accurate. I trust Don to support what he feels is best for our beloved town.
This is fantastic news! Don is a phenomenal choice for this ticket! A true family man, with a proven track record, and an unwavering love for the town of Westport, I’d be proud to call Don our 1st Selectman!
Yes! I’m thrilled that Don & Andrea are running. This team has the perfect combination of experience to lead and the skills to manage our town. They have built strong relationships within town departments and across all constituents. They know how to listen to multiple viewpoints, but importantly, they are each not afraid to make tough decisions to get things done. Westport’s future will continue to shine bright with them at the helm!
Don is an amazing choice for this position. He knows Westport and the intricacies of its politics better than anyone. He is pragmatic, sensible, and fair. He also cares about Westport and will do what is best for Westport.
This is great, but I’ll add…thank God for President Trump. How does that sound, Westport?
That sounds demented
Phil, Please ask Don O’Day that question. If I was a Republican, I know I would want that answered by the person heading up my party in my town.
Don, care to comment?
Last week when the Democratic P&Z members voted for The Hamlet you said political parties aren’t a thing in Westport.
Please be accurate. I wrote “On local matters like this one, party affiliation usually is irrelevant and a distraction.” Parties do matter in elections.
Don could have run as an independent, and with around 50% of voters in the last election listed as Independnt, he would have had a very good chance of winning.
Instead, he cast his lot behind a party led by a man which most Westport voters (71%) did not support. Once this goes national (if it does, as mentioned in the article) I would not want to be a member of the RTC who nominated a person who proudly states “I am not close to being a Trump supporter.” Could be a great local strategy. Brave? Maybe. But maybe also just desperate.
But let’s see what happens. I’m not claiming to be good at this. When I was 8, I thought McGovern was going to win in a landslide.
And don’t they have a town blog in Fairfield?
👌
Don O’Day can switch parties and pledge allegiance however he wants. It’s America, currently, after all. But his actions reveal his true allegiances. Those allegiances are to Don O’Day.
In January 2023, during the RTM vote not to overturn the Planning and Zoning Commission rezoning of Saugatuck, O’Day revealed what he thought of voters: “The majority of my District 3 constituents made it clear to me that they are against this proposal. But my job is to do more than read and respond to emails. It’s to make the best decision I can make, with the facts as I know them.”
As far as his airy, all-knowing, better-than-politics palaver, O’Day has already—during the first quarter of her 2026 campaign—contributed to Jennifer Tooker’s uphill campaign for governor.
He’s not partisan, except when he is. And he’s not a Republican, except when he needs a ballot line to run on.
Pick a lane. Don’t drive on the shoulder. Westport has had twelve years of mealy-mouthed, right-wing wrong turns. Not again.
Not an O’Day Moore.
Can’t let this happen Gloria. It’s as fishy as Tooker’s election.
O’Day’s patronizing comment about Kevin Christie tells me everything I need to know.
No thanks.
Westport has always chosen based on experience, qualifications, and long time residency.
As Andrea rightly pointed out, managing a town is akin to overseeing a corporation, involving a substantial number of direct reports, a budget, and numerous other responsibilities. Don has had the privilege of serving as the Board of Education and subsequently as a department head at a multinational financial institution.
Experience matters.
Leadership involves making tough decisions, knowing not everyone will be pleased, but conveying your thoughts and people respect that.
Don is a role model with quick, short, and sweet thoughts, eloquent voice, and peaceful, soft-spoken demeanor. I have learned a lot from him, and look forward to learning and absorbing more.
Unaffiliated with party, Don is Westport First. That’s not a party, that’s the people. This is how Westport runs.
Congratulations Don and Andrea. I have had the privilege of working with both Andrea and Don throughout my 14 plus years on the RTM.
Both Don and Andrea are proven leaders with track records in our town government of getting things done.
As elected officials, no one is getting paid, whether one is a registered Democrat, Republican, non-affiliated voter, or independent, we all work together to solve the task at hand.
Sidewalks, Downtown, Budgets, etc…we all get paid the same…$0. Political Parties don’t run Westport, people do.
Those who want to bring in party politics to our local election, please look to Hartford first, and see who is creating these crazy bills that become law that we, as a town must defend, and solve.
Thank you Don and Andrea for stepping up. Leadership and experience does matter.
Congratulations Don and Andrea! Both are proven leaders who are not focused on introducing partisan BS into the mix but doing what’s in the best interest of Westport overall. As an Independent, I am critical of both the Republicans and Democrats….what I am tired of is when each side can’t objectively look in the mirror and be critical of their own candidate’s imperfections. How the hell are we ever going to survive as long as we have a bunch of Bozos on both sides of the aisle never finding any compromise. We will all continue to be screwed!
And if O’Day, Moore get elected we are most definitely screwed.
They both are in unwavering lockstep with Tooker.
Another nightmare in the making.
Not once did Moore vote against Tooker. And she should have many times.
And not once did O’day ever not bend over backwards as an RTM ‘er to assist her with her horrible and nasty vindictive proposals, including the bullying of the few RTM who stood up for, and represented, the towns constituents, when ppl like O’day ignored their constituents in order to further Tookers ridiculous agendas.
Why would anybody be excited about this anti garden, anti business, and pro hamlet pair ?
This ticket is a Disaster.
Don and Andrea are an outstanding ticket – from either aisle’s perspective. See a large majority of comments here are positive with people able to see the bigger picture. Lots of long-term planning decisions required of our elected officials in the upcoming years. Would be prudent to have experienced people who have gotten things done in the chair. I’m an Indy and could care less about the party affiliation, and more about who will lead the town with a fiscally conservative, pragmatic vision.
Awesome! Don and Andrea are two Westport-minded people who have the experience, dedication, and community network to keep improving our Town. Fundamentally, these positions are about running the operations of the Town and having the community outreach connections to hear opposing views. Both have made hard decisions FOR WESTPORT, not themselves.
Anyone who has chaired the Board of Ed, volunteered for two major school committees, and makes a smart choice for his running mate has Westport’s best interests in mind.
Experience. Westport. Not “R” or “D” (or “I”)!
I don’t have a great view on Mr. O’Day or Mr. Christie yet and their qualifications. I respect their willingness to give to the town in terms of their time and experience. I also agree that most of the job is administrative and not political. That being said, I do find the “there’s no issue with pushing someone with an R in front of their name for this job” comments dangerous given the current state of the monolithic Republican party. All those “normal” Republicans in Congress voted for corruption in their cabinet officials, massive increases in ICE to enhance cruelty (Alligator Alcatraz) and the rest of the current budget which destroys health insurance for millions of Americans in order to lock in tax cuts for the wealthy. There’s also the general level of lawless, fact-less authoritarianism which is part of our current government. Basically zero Republicans have stood up and said “this isn’t what we stand for” and the ones that did then said they were retiring so they wouldn’t be ostracized. If Mr. O’Day is willing to sign up to be the standard bearer for the Republican Party in Westport, he owns these views until he publicly disavows himself of them.
Mr O Day. kindly answer. Do you support Trump and did you vote for Trump. ?
Thought it was pretty clear from the post that the last Republican Don voted for was Reagan and that he is ‘ not even close to being a Trump supporter.’ Great choice for Westport. Good luck, Don.
kindly let Mr O Day respond. He can be a leader and inform Westport if he voted for Trump or not.
Are you seriously suggesting that Dan made up these quotes from Mr. O’Day?
“In every meeting, I made it perfectly clear that the last Republican presidential candidate I voted for was Ronald Reagan, in 1984,” O’Day says.
“I am not close to being a Trump supporter. I’m a Westport supporter.”
Or do you need him to call you personally? But how would you know it was really him on the phone? Maybe he needs to meet you somewhere with 3 forms of ID? Take a lie detector test?
This is great news for Westport. I have known Don for decades and know him to make very thoughtful, practical decisions in the best interests of our town. His volunteerism for Westport speaks volumes to his commitment for our community; Chair of the BOE, Chair of CMS Building Committee, Long Lots BC, and RTM representative.
The ticket of Don and Andrea brings proven leadership and a nonpartisan approach for Westport.
Congratulations Don and Andrea!
This is horrendous news, and one can only pray they do not win, and that westporters have more sense.
Don and Andrea are almost without exception on the wrong side of every issue over the past 4 years.
A vote for O’day, Moore is just like a vote for Tooker.
Both are anti garden, pro destroying parking in the downtown, thus grossly anti business, and very pro Hamlet with both know many many of the investors. So if elected will go out of their way to cozy up to anything the Scamlet wants.
Both also pro the totally unnecessary 7 m dollar shed at Longshore etc.. that shed should be 1 million max.
Don is about as non transparent as it gets on every single issue, and is not only one of the rtm who voted to help Tooker on jesup green, but also he’s one of the RTM 29 who felt citizens be damned on petitions. How anybody thinks he is appropriate is just beyond me.
Let’s not forget he is pro hamlet and one of the reasons the text amendment did not get thrown out 2 plus years ago, when it should have, thanks to the persuasion and canvassing of the pro hamlet bully RTM’ers, who sadly persuaded the rest.
During her 4 years when Tooker wanted something passed ODay and a bunch of cronies on RTM instead of representing the views of those who elected them, bowed down to Tooker, without exception. It’s been PATHETIC to watch.
And not once in 4 years did Moore ever vote against Tooker.
A vote for these 2 is to vote for 4 more years of the same garbage.
A horrendous choice. I can’t think of a worse choice.
Any candidate would be better than 0’Day.
Check his and Moores record over the past 4 years.
It’s not pretty.
The Republican nominations sound good … as long as they truly are Republicans and support that credo. If they’re RINO’s (Republican in name only) just to be elected then that’s a sneaky way to be elected. Research their voting record is what all voters should do.
Diana, genuinely curious if you think a person who just became a Republican to run in a local race, hasn’t voted for a Republican in over 40 years and proudly states “I am not close to being a Trump supporter” can win as a Republican anywhere in this country right now. Its a fascinating move. Seems pretty RINO to me. But I’m just a dumb ass Democrat, what do I now.
WOW. That’s a story and a half above about the Most Wrong Person for the job!! Too much smoke.
Bottom line: If you get in bed with a Republican, then you are a Republican — and all Republicans owe fealty to The Man Who Wants To Be A Dictator & Said So Himself.
Are there no True Independents to run for 1st & 2nd???
That the Democratic candidate was steam-rolled by the BOE attorney makes this a I Would Vote For The Least Offensive Person in this instance. But, hey! Still working on keeping MAGA off the Clackamas County [OR] Commission again at next election so you are all on your owns.
Good grief. A third-rate opportunist who showed is colors during the Long Lots process. He’ll be about as responsive as the current FSW, who he is supporting in her run for governor. Enjoy your 4% O’Day tax increase, everybody.
On the other hand, his opponent is a guy who abstained from the vote on the employment status of the soccer coach because… he once watched a soccer game? This has yet to be very well explained.
Not exactly the best and the brightest. If nothing else, it is striking that the local GOP, having lost a BOE seat to a write-in candidate, is finding non-Republicans to run because their brand is so toxic.
Ride the Thunder
From Teddy Roosevelt’s “man in the arena:”
“…there are many who confine themselves to criticism of the way others do what they themselves dare not even attempt. There is no more unhealthy being, no man less worthy of respect, than he who either really holds, or feigns to hold, an attitude of sneering disbelief toward all that is great and lofty, whether in achievement or in that noble effort which, even if it fails, comes second to achievement. A cynical habit of thought and speech, a readiness to criticize work which the critic himself never tries to perform, an intellectual aloofness which will not accept contact with life’s realities—all these are marks, not as the possessor would fain to think, of superiority, but of weakness. They mark the men unfit to bear their part painfully in the stern strife of living, who seek, in the affectation of contempt for the achievement of others, to hide from others and from themselves their own weakness. The role is easy; there is none easier, save only the role of the man who sneers alike at both criticism and performance…
“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows the great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat…
“Perhaps the most important thing the ordinary citizen, and, above all, the leader of ordinary citizens, has to remember in political life is that he must not be a sheer doctrinaire. The closet philosopher, the refined and cultured individual who from his library tells how men ought to be governed under ideal conditions, is of no use in actual governmental work; and the one-sided fanatic, and still more the mob-leader, and the insincere man who to achieve power promises what by no possibility can be performed, are not merely useless but noxious.
“The citizen must have high ideals, and yet he must be able to achieve them in practical fashion. No permanent good comes from aspirations so lofty that they have grown fantastic and have become impossible and indeed undesirable to realize. The impractical visionary is far less often the guide and precursor than he is the embittered foe of the real reformer, of the man who, with stumblings and shortcomings, yet does in some shape, in practical fashion, give effect to the hopes and desires of those who strive for better things. Woe to the empty phrase-maker, to the empty idealist, who, instead of making ready the ground for the man of action, turns against him when he appears and hampers him as he does the work!”
Truths none of us should lose sight of, and that are particularly apt.
I have known Don O’Day the friend and neighbor, the husband, father and son, the professional, and the public servant, yes, Don O’Day the man, for nearly 30 years. Mr. Woog’s profile is accurate, but barely describes the heart and soul of a man that has fought tirelessly for our town, in general, and specifically for our children, particularly those requiring special education services and those with special needs.
He is the man for this moment in our town.
To O’Day and Moore, ride the thunder.