South Portland’s assistant city manager and economic development director is a finalist to become Portland’s next city manager.

Jon Jennings has been a top administrator for South Portland since 2013 and before that was president and co-owner of the Maine Red Claws basketball franchise.

South Portland City Manager James Gailey informed the City Council last Thursday that Jennings is a finalist in Portland’s city manager search.

“Knowing the dynamics of Portland and knowing Jon Jennings, I think he’d be an ideal fit,” said South Portland Councilor Tom Blake.

Jennings is one of three finalists. The names of the other two have not been confirmed.

When Portland last hired a city manager in 2011, the city made the names of finalists public and hosted a community reception to introduce them. This time, however, councilors and an outside consultant are keeping a tight lid on the finalists’ identities and have directed them not to comment on their candidacy until the city makes an announcement.

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Jennings did not respond to several requests for comment.

The Press Herald has been unable to reach a second possible candidate, an administrator in another Maine community who has been cited as a finalist by multiple outside observers. An elected official in the town where that person works said he had heard the rumor, too, but there has been no formal notification similar to the one in South Portland. The third candidate is from out of state, according to a city spokeswoman.

A hiring decision could be announced soon.

Councilor David Brenerman, chairman of Portland’s nominations committee, said the council has identified its top choice and he has been tasked with negotiating a contract with that candidate. He said that decision was made two weeks ago on a day when all three finalists visited the city for interviews with the council, city staff and a panel of residents, all of whom agreed to keep the names confidential.

The council met in executive session Friday to receive an update on negotiations, Brenerman said. He would not confirm whom the city was negotiating with, but was optimistic a deal would be reached soon.

“We’re pretty excited about the person we are negotiating with,” Brenerman said. “We’re pretty excited things will work out.”

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Don Jutton, president of New Hampshire-based Municipal Resources Inc., which was hired by the city to help with the search, said the firm has advised both the candidates and the city to preserve confidentiality throughout the entire process because the city might not be able to reach an agreement with councilors’ top choice.

“No one wants to be the second one invited to the prom,” Jutton said. “Until they announce it, there are three finalists.”

When asked whether candidates had been told by Portland’s council not to comment, Brenerman said, “I think we’ve suggested to them they might not want to comment until the process is over.”

Mayor Michael Brennan, who is leading the search committee, could not be reached for comment.

Whoever is hired as Portland’s manager will be taking over during a period of turnover and transition at City Hall.

The city manager and the assistant city manager jobs are vacant, and Police Chief Michael Sauschuck is serving as the acting manager.

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There has been significant turnover in the Health and Human Services Department, which has a new director, social services director and homeless shelter director. Also in recent years, the city has replaced its city manager, police chief, fire chief, finance director and human resources director.

And the new manager will take charge as the city and state are clashing over welfare spending. Changes in the state budget and assistance policies have caused the city to consider closing an overflow emergency shelter and to cut off General Assistance to asylum seekers starting July 1. Closing the overflow shelter could put 75 people on the streets, and the General Assistance change could affect more than 900 immigrants who are seeking political asylum.

Jennings was hired by South Portland in February 2013. Before that, he was president and co-owner of the Maine Red Claws from 2007-2012 and a general partner in the Thompson’s Point Development Co., which is undertaking an estimated $110 million redevelopment of nearly 30 acres of former industrial land along the Fore River.

Jennings spearheaded efforts to convince Portland councilors to give the project a 30-year, $30 million tax break to facilitate the development, which calls for an arena/event center that would become the new home of the Maine Red Claws, as well as up to 120 residential condominiums and a wide variety of other uses, including a circus school, office buildings, restaurants and an amphitheater.

He also served on the city’s Task Force to Prevent and End Homelessness in 2012.

From 2005-2007, Jennings oversaw Sen. John Kerry’s political operations in Massachusetts. He also served as an acting assistant U.S. attorney general and was a senior adviser for the White House’s Office of Cabinet Affairs under former President Bill Clinton.

Sixty-six people applied for the Portland city manager position during a nationwide search.


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