Jon Jennings has agreed to stay on as Portland city manager for an additional one-year contract, but intends to leave the post in 2022.

Jennings said in a written statement Friday that he will serve an additional year after his current contract expires in July 2021. He said the one-year extension will allow him to help the city navigate through the ongoing coronavirus pandemic and the subsequent financial impacts, which forced him and the council to close a projected $12 million hole in the current budget.

Portland City Manager Jon Jennings Derek Davis/Staff Photographer

“In light of everything the city is facing right now due to the pandemic and its impact on our fiscal health, I agreed to stay on for an additional year to assist the mayor and council as we continue to navigate these unprecedented times,” Jennings said.

Portland Mayor Kate Snyder said the council will likely begin the search for a new manager next fall. Snyder said she was grateful Jennings agreed to stay on so the council can conduct a thorough search and plan an orderly transition.

While the city manager has been criticized by progressive activists and others for some policy positions and budget decisions, the mayor and city councilors had publicly shown their support for Jennings in recent months.

“The council and I are grateful for Jon’s leadership and steadfast commitment to the city of Portland,” Snyder said in a written statement. “I look forward to continuing our work together as we respond to the myriad of challenges and opportunities.”


Jennings’ statement did not say why he did not seek a longer contract extension. He did not respond to an interview request Friday afternoon.

The one-year extension comes after the council conducted his first performance evaluation in three years.

It wasn’t clear if councilors raised any performance issues during the private review, or if they had hoped to sign a longer extension.

When asked whether anyone on the council wanted a longer contract with Jennings, Snyder said the manager was only open to one-year extension.

“He came into the evaluation requesting a one-year extension,” she said. “Because he was so clear about his intent, we had the opportunity to react to that intent and we agreed that a one-year contract extension was agreeable.”

City Councilor Spencer Thibodeau said the council’s primary goal was ensuring a steady hand as the city grapples with the uncertainty caused by the pandemic.


“We really were focused on having stable leadership for the next few years,” Thibodeau said.

Jennings became city manager in 2015. During much of his time as the city’s chief executive he feuded – both privately and publicly – with former Mayor Ethan Strimling.

Jennings was last reviewed by the council in 2016 and was rewarded with an $18,500-a-year raise. The following year, he received a three-year contract extension.

Last year, Jennings received a leadership award from the Maine Town and City Managers Association for the city’s response to the unexpected arrival of 450 of asylum-seekers. The city opened a shelter at the Portland Expo, collected nearly a million dollars in donations, and worked with area agencies and governments to find housing for the families.

However, Jennings has been the target of criticism from progressive activists, who frequently vilify him on posters, stickers and in email campaigns.

Over the summer, Black POWER demanded that the council fire Jennings, saying his policies hurt poor and marginalized people. But councilors quickly called a news conference to defend him.


The City Council is expected to vote on the one-year extension at its Nov. 9 meeting. Snyder said it does not include any pay raises.

Jennings had an impressive resume before being named manager in 2015.

He has a master’s degree in public administration from Harvard University and served as a senior adviser for the White House’s Office of Cabinet Affairs under President Bill Clinton.

From 2005-07, Jennings oversaw Sen. John Kerry’s political operations in Massachusetts. He also served as an acting assistant U.S. attorney general.

Jennings was president and co-owner of the Maine Red Claws, an NBA Development League team, from 2007 to 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.

He served as an assistant city manager in South Portland before crossing the bridge to take the top job in Maine’s largest city.


Jennings, who earned $185,000 last year, has been focused on boosting Portland’s reputation as an innovation hub, advocating for so-called smart city technology that would allow the city to pilot an autonomous driving shuttle service, traffic signals capable of adjusting themselves based on traffic patterns, free public wifi in certain areas and energy-saving LED street lights.

Despite criticism from Strimling and other community activists that Jennings was too involved in policy making, the majority of the City Council stood behind Jennings during his public feuds with Strimling.

Some did not like his outspokenness during the last year’s mayoral election when he spoke openly about wanting Strimling defeated. He appears to have gotten along well with the current mayor and most of the current council during the past year.

Jennings was quick to respond to the pandemic in the spring. He announced a state of emergency and curfews before the state acted and subsequently furloughed city workers to address a sudden drop in revenue. He was forced to redo his budget to address a project $12 million revenue shortfall, eliminating 65 positions with most of the layoffs coming from parks and recreation programming that was no longer taking place for public health reasons and not generating revenue.

City Councilor Jill Duson commended Jennings’ leadership in an interview Thursday, before the contract extension was made public.

“He’s been a good leader in tough times and that’s something I try to reflect to him every time I interact with him,” Duson said.

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