Choate Alumnus and Wallingford Mayoral Candidate Runs Again

Photo by Emily Ma ’25/The Choate News 
Wallingford resident plants pro-O’Connell sign outside their home.

Choate alumnus and Democratic candidate Mr. Riley O’Connell ’14 is relaunching his campaign to be the youngest mayor in Wallingford’s history. Notable, too, is that, for the first time in 40 years, incumbent mayor Mr. William Dickinson Jr. will not be the Republican candidate on the ballot.

Mr. Dickinson’s decision to forgo running for a 21st term has brought on a buzz of anticipation within Wallingford’s close-knit community. Residents are eagerly awaiting the voting period and impending results, which are scheduled for early November.

Two years ago, Mr. O’Connell launched a competitive campaign in the Wallingford mayoral election of 2021. He came closer to ending Mr. Dickinson’s historic term than any other Democrat had in the past three decades, losing the ballot by a margin of less than 400 votes.

If elected as mayor, Mr. O’Connell plans to modernize Wallingford through a series of public safety policies and initiatives. Bringing up the challenges that arise from a town with an outdated framework, he said, “We operate as if we’re in the 1980s, and it’s not healthy for a town to be stuck in a bygone era.” His agenda includes implementing direct deposit for town employees, installing a computer email for all workers, and introducing online bill payment options for residents.

Furthermore, Mr. O’Connell emphasized the pressing need for infrastructural improvements, from repaving roads to securing grant money for air conditioning in public high schools — a need highlighted by recent school closures due to high temperatures and a lack of working sustainable power.

A strong advocate for a forward-thinking approach, Mr. O’Connell aims to address more than just the immediate problems at hand. “Having a continuous, 15-year infrastructure plan is what my campaign proposes because, for the last 20 years, we’ve been without one,” he said.

In addition to his commitment to modernization, a primary focus of Mr. O’Connell’s will be to steer Wallingford toward a greener future. He hopes to increase the amount of renewable power sources and electricity, especially by prioritizing local solar initiatives. “There’s nothing prohibiting us from getting into the solar development business,” he said.

With Wallingford being one of three towns left in Connecticut to have municipal control of electricity, he believes that changes of power sources in the city are a fiscal responsibility that should be taken care of and would be easily achieved. “We’re in a unique situation in Wallingford,” he said. “[It] gives us a lot of independence to make decisions at the local level on how we want to be sustainable in energy usage.”

On September 14, Choate’s Young Democrats club hosted Mr. O’Connell for a “town hall session.” During the event, Mr. O’Connell offered students a closer look at his journey and campaign to bring Wallingford into the 21st century and participated in a Q&A session.

Vice President of Young Democrats Elia Ahmadi ’24 said, “Mayors are community leaders. They’re important leadership positions, and we wanted to give someone like [Mr. O’Connell] a platform.”

Ahmadi expressed admiration for Mr. O’Connell’s campaign: “[His] campaign is inspiring to us as students, especially as a young Democratic politician running in a city that has been historically Republican.”

According to Mr. O’Connell, his Choate experience played a pivotal role in his political career. “I first had no interest in politics,” he recalled. “I was not politically involved whatsoever stepping into high school.”

However, a class with HPRSS teacher Mr. Ned Gallagher transformed his perspective on government and fanned the flames of his budding interest in politics.

Academics aside, the relationships Mr. O’Connell cultivated at Choate continue to provide him with an enduring support system. “The friends that I made at Choate have played a huge role even now,” he said.

Many of his former classmates have supported his campaign. “I’ve had friends whom I haven’t seen since our high school graduation or the five-year reunion donate to the campaign,” he said.

Mr. O’Connell is confident that he and his campaign, many of whom are familiar faces he worked with two years ago, will be a stronger force in the mayoral election than they had been in 2021. He shared, “They have gained a ton of experience and gotten so much more comfortable with their jobs.” With an additional two years of political experience, he himself feels more comfortable with actively sharing his message by “knocking on doors, raising money, and hosting events.”

On the Republican side, current Town Council President Mr. Vincent Cervoni has secured endorsement as the official Mayoral Candidate from the Wallingford Republican Town Committee.

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