
WESTPORT — Westport Journal will sponsor a debate Oct. 16 between the three candidates seeking election to the office of First Selectman for the Town of Westport in November.
The candidates are:
- Kevin Christie, endorsed by the Democratic Town Committee
- Don O’Day, endorsed by the Republican Town Committee
- David Rosenwaks, endorsed by the Independent Party of Connecticut
Each has agreed to face off on Thursday, Oct. 16, in the Janet Hartwell Performing Arts Center at Greens Farms Academy, 35 Beachside Ave., at 6:30 p.m., doors at 6 p.m.
The debate, scheduled just over two weeks before the Nov. 4 election, is open to the public. The event is free but advanced reservation is required. Click here to register.
Voters are encouraged to forward questions for the candidates to publisher@westportjournal.com
The debate will be moderated by Jeff Wieser. Wieser is a former corporate banker and non-profit CEO and also the moderator of the Westport Representative Town Meeting. He is an ongoing advocate for the benefits of providing suburban housing to the homeless.
“Westport Journal is excited to take an active role in helping voters understand how the candidates differ on how the folks inside 110 Myrtle run the town,” said Doug Weber, Westport Journal’s Publisher. “From parking and traffic to budgets and taxes, parks and public works, the First Selectman oversees a lot of important town functions.”
Kevin Christie spent over 15 years in finance, investment banking, and corporate strategy at IBM, Merrill Lynch, and The Madison Square Garden Company. He advised CEOs and boards, led cross-functional teams, and executed over $40 billion in strategic and financial transactions. Kevin currently serves on the Westport Board of Education, to which he was elected in 2021. Kevin has lived in Westport since 2018.
Don O’Day retired after a 40-year career in financial services, including 35 years at Citi, where he held many senior roles in the mortgage business. He has spent the last 20 years in a variety of town-wide roles–on the Board of Education, Coleytown Middle School Building Committee and the Long Lots School Building Committee. He is currently a member of the RTM. Don has lived in Westport for more than 30 years.
David Rosenwaks spent a decade on Wall Street, first at Solomon Smith Barney and then at his own firm. After selling his share in the business, he pursued his passion for music, launching a second career as a singer-songwriter. After his move to Westport five years ago, David was elected to the RTM, where he serves on several committees. He serves on the Westport Arts Advisory Committee and the PTA Council.
The event is free but advanced reservation is required. Click here to register.
Westport Journal LIVE is underwritten by the KMS Team at Compass.

A debate with candidates for the Board of Education with a focus on the state of special education is needed. This is a large portion of the school budget. Studies need to be conducted to assess the return on investment, the efficacy of the current system, accountability and true parent involvement. Too many children are simply being passed through from grade to grade. We need a system overhaul to ensure they strive, are successful and do not merely survive K-12 education. Check the CT Board of Education statistics on how Westport has been doing with special education. Your tax dollars are not being well spent.