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Jill Dillon defies odds, secures seat on Westport Board of Education

Photo contributed by Jill Dillon
Jill Dillon and her team members stand outside in their logowear in order to spread the word about their campaign and educate voters about what makes their policy agenda unique.

After the deadline had passed to run on the election ballot, Jill Dillon received a phone call from an unknown parent. Little did she know that this single phone call would give her motivation to run for the Westport Board of Education (BOE). As a former PTA president, a politically active town-member and a mother to students in the Westport school system, Dillon knew that she not only had the experience to serve on the Board of Education, but also the means to do so. 

The Board of Education is responsible for the operation and maintenance of the Westport Public Schools. Their job is to prioritize the well-being of students, improve academic quality and support faculty. 

“Beyond having been a two-time PTA President, I volunteer a lot of my time in the community,” Dillon said. “So I know a lot of people around town from my various volunteer endeavors.”

Before Dillon’s nomination, the town structure would have required either two Democrats and one Republican to be elected to the board, or two Republicans and one Democrat. There was growing concern over the two Republican candidates due to their ideological beliefs and extreme policy agenda. 

“[The Republican candidates were] saying that [the Board of Administration] was grooming our children, that the schools were indoctrinating the children with a woke, leftist agenda,” Dillon said, “and they asserted, without proof, that academics were suffering as a result of the district’s focus on [diversity, equity and inclusion (DEI)] and social emotional learning.”  

If Dillon did not run, one of these candidates was guaranteed a seat on the board, even if the two Democratic incumbent candidates Lee Goldstein and Neil Phillips won. 

After receiving a phone call from a stranger encouraging her to run as a write-in candidate, Dillon ultimately decided to launch her campaign.

“I figured if a stranger was asking me then there must be others out there who felt as strongly as he did,” Dillon said. 

She sought advice from a dear friend, Patra Kanchanagom, and they decided that if no one tried, they would later kick themselves. Kanchanagom became Dillon’s campaign manager and they recruited a few more members on the way. 

Jill had an incredible core team of volunteers and our amazing community cheering us on. This campaign was successful because so many people in our community were motivated and energized. They texted, called, emailed and spoke with friends and neighbors.

— Patra Kanchanagom, Jill Dillon's campaign manager

On Oct. 12, the day of the BOE debates, Dillon made the decision to run. She quickly made a logo, bought a t-shirt and some iron-on printer paper from Michael’s and made a homemade t-shirt. That evening, she went to the debate wearing her shirt and stood outside, telling people that she was running as a write-in candidate. Dillon was joined by her husband, the parent who had called her and some of her friends. 

“Our top priorities with the campaign were getting the word out about Jill’s candidacy and educating the public about how to write in a candidate,” Kanchanagom said. “We knew from the beginning that it would be an uphill battle to get Jill elected because we didn’t have a political party behind us with a seasoned apparatus to get things done.”

On top of that, Dillon’s team was asking voters to go to the polls with a plan to write her in, which is something that many voters have never done. 

Through the use of social media, lawn signs and public discussion, Dillon’s team successfully spread the word about their campaign. On Election Day, they were cautiously optimistic about their prospects of winning. None of them had ever run a campaign before, so they didn’t know what to expect. However, they believed in Dillon. On Tuesday Nov. 7, Dillon secured her seat on the Board of Education. 

“Jill had an incredible core team of volunteers and our amazing community cheering us on,” Kanchanagom said. “This campaign was successful because so many people in our community were motivated and energized. They texted, called, emailed and spoke with friends and neighbors.”

Dillon’s success story is proof that grassroots efforts can spread like wildfire when voters are active, passionate and determined. Democracy allows for the people to decide who represents them, and Dillon’s campaign gave voters the chance to change the course of the election.

“I think I am a strong addition to the Board of Education in my own right, given my experience and passion for the town and our schools,” Dillon said. “The energy at the polls that day was palpable and I was thrilled to be a part of it.”

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About the Contributor
Ruby Kantor ’24
Ruby Kantor ’24, Paper Managing Editor
Inklings Paper Managing Editor, Ruby Kantor ’24, claims she decided to join the paper for many different reasons.    “I really liked the different style[s] of writing that journalism [offered],” Kantor said when prompted with why.   “It's a great way to build new community and meet new people,” Kantor said.   However, journalism is not the only thing she’s had to tackle recently.  Over the summer, she took on the challenge and, at times, “dreaded experience” of being a children’s camp counselor.  “It was exhausting,” Kantor said with a smile, “but the kids were very cute, and it was worth it.”

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