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Jason Rogers stepped down from his role as Naples’ town manager on Tuesday, May 20. After a tenure of just 19 months, he is handing off the reins to Treasurer and Road Commissioner Randy Lessard, and moving to Florida to pursue the next chapter of his life.

Rogers said he had moved to the Lakes Region shortly before becoming town manager, and that his role in Naples was his first experience in municipal government. Before that, he had served in the Navy for 32 years, and he credited his experience in command as being instrumental to helping him transition into running a small town.

Rogers described the overall experience as “great,” and praised the people of Naples as being “amazing.” He said that, while people were not always happy with the decisions he made, at the end of the day, he felt that the decisions that were made in collaboration with the Select Board were the best for the town.

Rogers also spoke about some of the challenges that he faced as town manager. His biggest challenge was understanding the needs and wants of residents. In particular, he noted the difficult tightrope he walked between preserving the rural feel of the town, while also implementing improvements and modernizations that could continue to attract newcomers and tourists to the heart of the Lakes Region.

Regarding his decision to step down, Rogers said that he was contacted by some friends in Florida who offered him the position of CEO of their company. After much consideration, as well as consultation with his wife, they made the decision to move to Florida.

Rory, an experienced reporter from western Massachusetts, joined the Maine Trust for Local News in October 2024. He is a community reporter for Windham, Raymond, Casco, Bridgton, Naples, Standish, Gray,...

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