The road to victory for a write-in candidate is daunting.
First, voters have to know he or she is running. They must learn how to fill in the ballot. At the polling place, they have to remember to do it.
Meanwhile, the candidate must somehow get his or her message out — without relying on traditional party machinery.
There’s a reason why Westporters cannot recall the last time — if ever – such a candidate won office here.
But Jill Dillon is undaunted. She’s running a write-in campaign for the Board of Education.
Jill Dillon
And she thinks she has a shot.
The long-time unaffiliated voter decided to run when she realized that because the Town Charter limits one party to no more than a bare majority on the BOE, one of two Republican candidates — Camilo Riano or Jamie Fitzgerald — seemed guaranteed a seat.
Their views worried Dillon, who served as PTA president at both Kings Highway Elementary and Coleytown Middle Schools, and generally supports the Westport Public Schools’ administrators and teachers (and the current Board of Ed).
Without speaking with Democratic Town Committee representatives, her hope was that voters would circle the names of Lee Goldstein and Neil Phillips — the 2 incumbent Dems in the race — and also bubble in the bottom of the ballot, then write “Jill Dillon.”
Her decision to run was solidified by support from friends — and strangers.
But “thank you for running” comments don’t translate into action. So Dillon and a dedicated corps of volunteers have been hard at work. They’re using social media, word of mouth, meet-and-greets and more.
Like all candidates, Jill Dillon has plenty of lawn signs.
Besides the usual challenges — including not appearing in the League of Women Voters’ guide — she has had to answer questions about why one of her 2 daughters attends private school. (The other is at CMS.)
“It was the right decision for her,” Dillon explains. “People assume we thought Staples was deficient.
“Not at all. As parents, we all make the best decisions we can. We thought that environment was the best fit. It’s been very good for her.
“I love our schools. I am 100% committed to Staples, and the Westport Public Schools.”
Criticism has not bothered her.
“I know who I am, and who I am not,” Dillon says. “Name-calling doesn’t bother me.”
She does not engage in back-and-forth on social media. “It degenerates quickly” into personal attacks, she says.
“It’s ironic. We don’t want our kids to be bullies. But adults bully all the time.”
Democrats Goldstein and Phillips have been called names. So have Republicans Fitzgerald and Riano.
“You can disagree strongly with what they says,” Dillon notes of the GOP candidates she is running against. “But calling them names takes away from their arguments.
“I don’t think I’ve smeared Camilo. I’ve stated his positions, and where I disagree. I think I’ve provided factual evidence to back up my claims.”
As her campaign heads toward the November 7 election, Dillon has been surprised by support from people she does not know.
Wearing a t-shirt with her name at CVS, she was approached by a woman with young children. “Thank you for giving us a choice,” she told Dillon.
Jill Dillon with supporters, at the Westport Farmers’ Market.
It’s one thing for a write-in candidate to forage for votes in areas where she’s known — like parents with children in schools. But Dillon realizes she must get the word out to other groups, including older voters, empty nesters, and younger voters without children.
So she and her volunteers continue to post on social media. They hand out yard signs.
And they keep hoping that voters know there’s a bubble at the bottom of the ballot that must be filled in, with a name they remember.