A new chapter
By Amy Wu, 11.7.2025. CT EXAMINER
MYSTIC — Bill Middleton’s 60th birthday turned into an even bigger celebration this year. The day before, he clinched Stonington’s first selectman seat in a landslide win and marked the occasion surrounded by family, friends and supporters at the Jealous Monk.
Middleton, who ran as an unaffiliated candidate and was endorsed by the Democratic Party and Connecticut Forward Party, thanked voters at the Tuesday gathering and said he’s “looking forward to going into a smooth transition and keeping up the momentum.”
Middleton plans to hit the ground running when he’s sworn in on Nov. 18. During a two-week transition period, he plans to meet with outgoing First Selectman Danielle Chesebrough, who has held the position since 2019. Chesebrough has said she will be focused on growing the Connecticut Forward Party, which she chairs, and projects at the United Nations, where she previously worked.
The Connecticut Forward Party endorsed Middleton along with Deborah “Deb” Norman, who won the selectman seat, and campaigned alongside Middleton.
“I’ll be talking and meeting with Bill in terms of budget to get him to get him up to speed,” Chesebrough said.
Chesebrough, who ran and won as Forward Party candidate in 2023, said she’s excited that Middleton is on board.
“I think it’s great for the Stonington community. They’ve had six years of me being unaffiliated and that type of leadership,” she said, adding that she’s hopeful there will be a similar type of leadership will continue, especially as Middleton is also unaffiliated.
A new chapter
Since hitting the campaign trail in August, Middleton has been wrapping up existing projects to make room for his new chapter.
Middleton, a Mystic resident who owns several restaurants downtown, said restaurants “kind of run themselves” with a solid business management plan. Another project — a $2.5 million renovation of a 1965 mid-century motel into a 56-room hotel called The Commodore — is expected to be done by the end of the year.
Middleton will also step down from the Police Board of Commissioners and remain on the board of the Mystic Aquarium and The James Merrill House Foundation.
Middleton said his experience running businesses and serving on a range of boards will help him in the new role. Before starting Cannonball Management, which operates restaurants in Mystic, he spent 25 years in the investment business industry, including at Federated Investors. He launched and later sold his firm Sound Portfolio Advisors.
“People look for …