SOUTH PORTLAND — City Manager Jim Gailey surprised and saddened many at City Hall on Wednesday when he announced his resignation to take the assistant manager’s position for Cumberland County.

Mayor Tom Blake said the City Council will act quickly to replace Gailey, but he expects it to be a challenging task, especially with the dissent that has troubled City Hall in recent months. Gailey is a native son who started working for the city nearly 30 years ago and has overseen its 295 municipal employees for nine years.

“His passion and historical knowledge and caring for this city will be almost impossible to replace,” Blake said. “We both got a little teary eyed today when he told me.”

The council will hold an executive session at 5 p.m. Monday to develop a plan to replace Gailey and cover his duties in the interim, Blake said.

Josh Reny, who became assistant city manager and economic development director in late September, will likely serve as interim city manager, Blake said.

“We’re going to move as quickly as we can and go far and wide to bring in the best person possible,” Blake said. “I don’t expect to see too much disruption – though we have several new department heads – because Jim surrounded himself with good people.”


Gailey announced his resignation 45 days before his intended departure, as required by his contract, according to his resignation letter to Blake.

Gailey will replace William Whitten, who retired from the assistant county manager position June 3. He was hired from among 39 applicants by County Manager Peter Crichton, with help from a search committee and the approval of county commissioners.

“Jim is an outstanding choice. His qualifications speak for themselves,” Crichton said, noting Gailey’s varied resume, including several city jobs since 1995.

The county has a $40 million annual operating budget and 430 full- and part-time employees. Crichton said Gailey will oversee emergency management services, information technology, facilities and capital improvements, community development and the Registry of Deeds, as well as public, municipal and legislative relations.

Gailey, 45, will start his county job in late July, Crichton said. Whitten’s annual salary was $96,000. Gailey will be paid $106,000 per year. Gailey’s annual salary as city manager was $121,000, plus a monthly vehicle allowance, Blake said.

Gailey, who was named Manager of the Year by the Maine Town and City Managers Association in 2014, declined to be interviewed for this story. “I don’t like talking about myself,” he said in an email.


Blake described Gailey as an excellent money manager who has led the city to top credit ratings while overseeing a $31.4 million annual municipal budget, as well as a team leader with a knack for hiring good people.

But the job has grown exponentially more difficult in recent years, Blake admitted, especially with petroleum-related controversies in the community and on the council. Conflicts included the failed waterfront protection ordinance referendum in 2013 and the subsequent passage of the Clear Skies ordinance to block the reversal of the Portland Pipe Line Corp.’s flow of oil. The ordinance is now being challenged in federal court.

More recently, some councilors and their supporters have flouted tradition and council rules, disrupting public meetings, intervening in municipal operations and flooding Gailey, city employees, councilors and the city’s lawyers with emails providing and demanding additional information.

“The divisiveness has been awful the last three years and it has intensified over the last six months or so,” Blake said. “Jim being at the helm, he couldn’t help but bear the brunt of it, but he did a great job through all of it.”

Councilor Claude Morgan said Gailey has had “a very tough year, there’s no question about it. But his performance has been spectacular, as it has been for years. With him, the city always came first. I’m heartbroken that he’s leaving us.”

In his letter to Blake, Gailey said he started working for the city “as a high school kid refereeing recreation soccer games.” In 1995, with a bachelor’s degree in geography from the University of Maine at Farmington, “I was fortunate to turn a college internship into my first full-time position here in South Portland and I never looked back.”


Before becoming city manager in 2007, Gailey held several municipal positions, including assistant city manager, community development director, building site planner and property tax specialist. In 2001, he received a master’s degree in planning and policy analysis from the Muskie School of Public Service at the University of Southern Maine.

“A lot has changed since the fall of 1986 and the experiences and opportunities that I have had working in six departments along the way are amazing,” Gailey continued. “I now find it’s time for a change as I want to explore other opportunities and career goals.”

Gailey, who grew up in South Portland and lives in the city with his wife and two children, thanked the council “for the opportunity to serve this great city. I worked with a number of excellent city councilors over the years and I am truly grateful.”

Gailey also thanked “the 295 city employees who make this community a terrific place to work. They are the deliverers of service and are the faces of our community. We had a lot of fun doing a lot of great things here in South Portland and this will not change because one person is gone. I wish you all the luck.”

Kelley Bouchard can be contacted at 791-6328 or at:

[email protected]

Twitter: KelleyBouchard

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