The Board of Education election just got even more interesting.
Jill Dillon — a well-known former PTA president, St. Luke religious school teacher and community volunteer — has launched a write-in campaign.
Her goal is to prevent the election of at least one — or possibly both — Republican candidates to the board.
The Town Charter prohibits any political party from having more than a bare majority on the Board of Education — in other words, no more than 4 of the 7 seats.
Three seats will be filled next month. The Democratic and Republican Town Committees picked 2 nominees each. Before Dillon’s entry, that meant that at least one of the Republicans — Jamie Fitzgerald or Camilo Riano — would be guaranteed a seat.
Riano attends most BOE meetings, where he often criticizes the board. Little is known about Fitzgerald, who has never run for office.
Dillon has been an unaffiliated voter since she and her husband John moved to Westport in 2012. Raised in Virginia by Republican parents, she says she has voted for candidates from both parties in local elections.
Party labels, she says, “can put people in a box. That does a disservice to everyone. As an adult, I look at issues critically, and on my own.”

Jill Dillon
Dillon had not liked Riano’s confrontational tactics during BOE public comment time. She says she withheld judgment about Fitzgerald, hoping to learn more about her stands.
But after watching two “fireside chats” produced by the RTC, she became concerned about the future of the Board of Ed if even one of the pair was elected.
As PTA president at both Kings Highway Elementary and Coleytown Middle Schools, she has watched the BOE operate.
“The current board is excellent,” Dillon says. “They are congenial and collaborative. They get things done. They work well together, and they have a good relationship with the administration.”
As she learned more about Riano and Fitzgerald, and talked with friends who were also concerned, she considered a write-in campaign.
Last week — just before the League of Women Voters debate with Riano, Fitzgerald and Democratic incumbent candidates Lee Goldstein and Neil Phillips — Dillon got a call from a man she did not know.
He’s a Saugatuck Elementary School dad, he explained. He heard she might be running, and urged her to do so — to “keep the Board of Ed moving forward.”
That night, she attended the LWV debate. She wore a t-shirt with a logo a college friend had quickly designed. She attracted plenty of interest — and encouragement.

Jill Dillon’s logo
As she listened to the debate, her decision to run was solidified. She had served as a PTA president the same time as both Goldstein and current Republican BOE member Dorie Hordon. Dillon realized she could help them both keep the Board functioning in a forward-looking way.
“Debate Camilo and fireside Camilo are not the Camilo who shows up at Board meetings,” Dillon says. “He’s combative. He comes at issues in a way that makes people not want to engage.”
Fitzgerald, meanwhile, “did not show depth of understanding about our schools.”
Neither Republican candidate, Dillon says, “seemed to care about the mental health of our kids. Jamie talked about her 30-year-old daughter who was bullied in 6th grade, but didn’t seem to think we should focus on bullying and mental health.
“Camilo said his kids are happy. I’m glad. But I’ve seen a lot of kids who are struggling. Your kids may not be, but others are. And kids who seem happy may not always be.”
Dillon’s professional career was in public opinion research. Moderating focus groups, she led discussions and helped leaders make informed decisions.
She had her first daughter at 35. After CMS, she is now a freshman at an all-girls school.
“As parents, we all make the best decisions we can,” Dillon explains. “We thought that environment was the best fit.
“I love our schools. Not continuing to Staples was hard for her, and me. I’ve known the (current) freshmen since they were in kindergarten.
“She still sees her friends every day. And her school has been really good for her.”
Dillon’s other daughter is a 7th grader at Coleytown Middle. “She wants to go to Staples. Every kid is different. We’ll see what works for her,” Dillon says.
Running as an unendorsed candidate is a challenge. The bottom of the ballot has space for write-ins. Dillon will register with both the Secretary of the State and Town Clerk, so they will understand the intent of voters who write not the preferred “Jill Dillon,” but something like “Jill D,” or misspell her name. Voters must also fill in the circle next to that write-in name.

Dillon has not spoken with the Republican or Democratic Town Committees. She has heard that Democrats are pleased there may be an alternative to Fitzgerald and Riano, if both Goldstein and Phillips are re-elected.
She and her “scrappy team” will spend the next 3 weeks knocking on doors, making calls, and educating voters on how to write her name on the ballot. “Fill in Dillon” has a nice ring, she laughs.
Tomorrow (Tuesday, October 17, 7 p.m.) she will meet voters in Westport Library Room 215.
On Friday (October 20, 8:30 to 10:30 a.m.), she’ll host an informal gathering at the Compo Beach pavilion.
“Our town boards operate wonderfully,” Dillon says. “Party affiliation hasn’t meant much here. Local issues haven’t fit neatly into a political box. This is the first time where an election might impede progress.”
But local issues are important. On the Long Lots Elementary School renovation project — which has become tied to the fate of the Westport Community Gardens — Dillon says, “we need a new school, full stop. And the gardens are gorgeous. They’ve provided so much. They’re part of the fabric of Westport. We have to try hard to find a way to build both.”
Regarding the display of LGBTQ-themed books challenged at Staples (which Riano and Fitzgerald have criticized, and Goldstein and Phillips supported), Dillon says, “It’s a difficult needle to thread. I understand parents’ objections to the display, and to the pictures and content of some of the books.
“But it goes back to mental health. When kids feel different, they can’t learn well. If one child needs those books, I want them available. There can be a happy medium between banning books, and exposing kids to content their parents don’t want them to see.”

Candidates at Thursday’s League of Women Voters debate. From left: Lee Goldstein, Jamie Fitzgerald, Camilo Riano, Neil Phillips. (Photo/Mia Bomback)
Of her decision to run, Dillon says, “I have immense respect for all members currently serving on the Board of Education, regardless of their party affiliation, and I hope that Lee Goldstein and Neil Phillips are re-elected.
“I think it is imperative that the third seat go to a candidate with a moderate voice who has publicly demonstrated collaboration, been an active leader in the community, and who cares deeply about the continued excellence of our schools. I am that candidate.”
She adds, “Westport’s schools are our crown jewel, and it’s the BoE’s responsibility to lead the way. Our schools offer unparalleled access to learning, athletics, and the arts, while fostering community.
“Our children’s education is the foundation from which they are launched to achieve success in a broader world.”