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.
