Jay Gill

Jay Gill set to leave Winchester in early January

WINCHESTER - 2023 is shaping up to be the year of change in Winchester. DPW Director Jay Gill, Fire Chief Rick Tustin and Town Planner Brian Szekely all plan to move on at (or just after) the end of the year. The town is also searching for a permanent town manager (who may or may not be current interim Town Manager Beth Rudolph).

For Gill, although rumors of his departure circulated back in the summer, Town Moderator Heather von Mering officially announced to Town Meeting several weeks ago he would be leaving. Just recently, he told The Daily Times Chronicle his last day will be Friday, Jan. 6.

He would have left earlier, but he decided to hang around a little longer due to all the construction projects going on in town. In fact, Gill called it the “busiest construction season of his career.”

Most of the projects seem on schedule and on budget. Gill said the 115kV Eversource project just finished in Winchester with only a few loose ends to tie up. Some of the streets that Eversource opened have already been repaved.

During his nearly four decades in Winchester (Gill became acting DPW Director in August of 2011, taking over for Ed Grant, before becoming the full-fledged director when Richard Howard took over as town manager in 2012) Gill saw a lot including, according to him, more than 1,000 inches of snow (this includes Nemo, the blizzard, not the movie, dump two feet of snow in Winchester back in February of 2013).

In fact, Gill said he only missed two big snow storms. One time he received a call from former Daily Times Chronicle editor Chris Connelly while he was on vacation in Florida with his family. Talk about a lucky break.

Now that he’s officially moving on, Gill wanted to thank all the DPW employees he’s worked for and with in his 39 years in Winchester. He started with the public works department back in 1983. Today, the department is actually 58 percent smaller than it was back then.

While the DPW remains understaffed, Gill said everyone does a “fantastic job” and he’s been “very lucky” to work with such dedicated people.

Once he leaves the DPW, Gill plans to keep working. He began his career with Winchester at 21 years old making $7 per hour. He’ll leave after 39 years making slightly more.

He’s proud of the work the department did on all the fields including the recent work at Manchester Field (getting the field ready for the Thanksgiving Day football game), Bellino Park, the high school, and all the flood mitigation projects.

He called leaving “emotional” and said he would miss the people he’s worked with, but he’s happy for the opportunity to spend more time with his family. In fact, he mentioned going to Disney World as a retirement gift.

Taking over for Gill, at least on an interim basis, will be Operations Manager Mike Wise, a 30-year employee whom Gill referred to as “very capable.” The next town manager will choose Gill’s permanent replacement.

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