Westport’s interesting race for 1st selectman just got even more intriguing.
David Rosenwaks will be the town’s first-ever Independent Party-endorsed candidate. Having secured more than enough signatures, he’ll have his own line on the November 4 ballot.
He joins Democratic-endorsed Kevin Christie, and Don O’Day, the Republican-endorsed candidate who is now unaffiliated.
Rosenwaks, 48, spent 25 years as an unaffiliated voter. He became a Democrat less than a year ago, but is now joining the Independent Party.
David Rosenwaks
Party politics is one of the reasons Rosenwaks is running for the town’s top job. A first-term member of the non-partisan Representative Town Meeting, he says, “I want to change the tenor of town government. As an Independent, I’ll answer to one entity: Westport and its citizens.
“A lot of decisions have been made before weighing all views. A lot of people feel unheard and undervalued.”
Rosenwaks envisions a return to former 1st Selectwoman Diane Farrell’s “Brown Bag Lunches.” A member of the RTM’s Information Technology Committee, he also hopes to “modernize and digitize” the town’s technology system.
Rosenwaks and his wife, actor Liz Fye, moved to Westport from New York at the beginning of COVID. They felt “blessed” by the school system, Library, beaches and rich arts heritage.
Rosenwaks dove into all aspects of the town. He attended commission and TEAM Westport meetings, Westport Library events, the Senior Center, the Westport Country Playhouse and more. He is a member of the Westport Arts Advisory Committee, joined the Citizens Police Academy, served on the PTA Council in a technology role, and coached recreation soccer.
“I learned a lot from the people who have been here for years,” Rosenwaks said. “They helped me understand how this town grew and evolved into what it is now.”
At the same time, he says, “Westport is at an inflection point. The average age is 39 to 45, depending on the data you use. We’re ready for the next evolution of the town. I’m confident I can be the bridge between those who have been here for decades, and the more recent arrivals.”
His RTM District 6 race was very competitive: 7 candidates for 4 seats. He knocked on 700 doors, and heard a diversity of viewpoints on a variety of topics.
David Rosenwaks
In the past 5 years, Westport has grappled with some major controversies.
Rosenwaks — a Long Lots Elementary School parent — was disturbed by the overcrowding and neglect at his children’s school. At the same time, he says, “the Community Gardeners should have been handled differently. They deserved a more honest approach up front.”
Redistricting 30 children “across the river, at 2 of the worst times of day” was an example of decisions being made “piecemeal, not holistically,” he says.
Rosenwaks was also disturbed at the Board of Education’s handling of Staples High’s soccer coaches.
“Over 100 kids sat in Town Hall for 14 hours,” he says. “Their voices were not heard. They were disilliulsioned. That’s a problem for their future, and the future of the town.”
As for the Hamlet, he says, “the majority of people in Westport want some development. But not to the extent of what was proposed. How did we get here, held hostage by a developer that doesn’t connect with what most people want?”
after graduating from Dartmouth College, Rosenwaks joined Salomon Smith Barney/Citigroup as an investment banker.
He then co-founded a multi-billion dollar asset management firm, StoneCastle Partners. After selling it a decade later he pivoted to singing, songwriting and art collecting.
He’s recorded with Paul Shaffer and Phil Ramone. Rosenwaks’ original music has appeared in independent films. He headlined shows at the Public Theater, Joe’s Pub, and BB King’s.
Now, he says, “I spend most of my time dedicated to the town.”
Which brings him back to the reason he is running.
“I want what’s best for my family, my neighbors, and the town of Westport,” Rosenwaks says.
“I want everyone to feel involved. Whether it’s Jesup Green or a parking lot, every decision should be about what’s best for Westport.”
To run on the Independent Party line, Rosenwaks needed signatures from 1% of the number of people who voted in the previous selectperson’s race: 85 registered voters.
He submitted 132.
Now he awaits official certification, from the Independent Party.
He is running solo for the top spot. According to the Town Charter, if a person elected 1st selectman “has not been nominated by political party, the 2 defeated chandidates for First Selectman having the high number of votes shall be elected Selectman.”
It is unclear if that means the 2nd and 3rd selectmen would be the 2 other candidates for that position (Christie and O’Day, in whichever order they finish), or if the candidates of the runner-up party with the most runner-up votes would serve as 2nd and 3rd selectpersons, respectively (Christie and Amy Wistreich, or O’Day and Andrea Moore).
Either way, Rosenwaks says, “I will be happy to work with any combinatiion of ‘defeated candidates. Leadership comes from the top.”
