Jon Jennings decided in June to leave his post as Portland city manager before his contract expires next summer.

Voters had just elected a charter commission charged with recommending changes to the form of government. One newly elected commissioner posted a social-media warning to Jennings on election night, saying he was going to lose his job and be “the last white supremacist city manager.”

Jon Jennings speaks to the Portland City Council after members voted in favor of approving him for the city manager post in 2015. Derek Davis/Staff Photographer

When asked about it, Nasreen Sheikh-Yousef asserted again on social media that Jennings was a white supremacist and that his position should be abolished.

Jennings said he was offended by the charge because he had never spoken with Sheikh-Yousef, who did not respond to an interview request for this story.

Jennings had spent his career working in professional sports with people from diverse backgrounds, both as an assistant coach for the Boston Celtics and founder and general manager of the Maine Red Claws, and created the Team Harmony Foundation to bring young people together to stand against hate and bigotry. He supported the creation of the city’s Office of Economic Opportunity, which aims to help new Mainers enter the workforce.

But what upset Jennings most, he said, was how the comment affected his teenage daughter, who implored him to find another job so they could move as soon as possible. He took her advice and landed the city manager job in Clearwater, Florida. Monday was his last day as Portland’s city manager. Danielle West, the city’s attorney, is taking over as interim city manager while the council conducts a search for a permanent replacement.


In a wide-ranging interview with the Press Herald, Jennings reflected with mixed emotions on his tenure.

“I’m quite incredibly proud but also profoundly disappointed with where the city is going politically,” said Jennings, who previously served under President Bill Clinton as a senior adviser to the White House Office of Cabinet Affairs and oversaw Democratic Sen. John Kerry’s political operations in Massachusetts. “When I hear people labeling me or labeling others, it’s just a sad time we’re living through. I think the sadness I feel for Portland is I saw a lot of this hateful commentary in Washington.”

When he interviewed for the Portland position, Jennings said that he intended to be a “strong manager,” one who would insulate staff from political pressure so they could focus on their daily responsibilities and work toward the collective goals of the council, rather than for individual councilors.

City Hall had seen a tremendous amount of turnover of both department heads and rank-and-file staff, partly because of the political pressure from elected officials pursuing their own agendas, he said.

“I asked (councilors) to raise their hand so I could see they heard me and were serious about it,” said Jennings, who was selected unanimously in June 2015 to be the city’s fifth manager in four years.

Since then, Jennings has lived up to that strong-manager promise. In the process, he has become public enemy No. 1 for progressives, who want a city of 68,000 people to more aggressively confront systemic nationwide issues of poverty, affordable housing, homelessness, social justice and racial inequality. At the same time, he has received steady support, and generous salary increases, from the councilors who have employed him.


Portland’s city manager is charged with implementing a $268 million budget, managing a workforce of about 1,400 employees and taking orders from elected officials in a city that contends with complex social and economic issues in addition to providing basic municipal services to the mainland, islands and an international airport. Jennings has long seen increases in city budgets and property taxes as playing a role in the city’s overall affordability problems. He’s kept his eye on the bottom line.


“My position is about governing,” he said of the city manager’s job. “It’s not about politics, and that is, I think, the frustration people on the extreme left or the extreme right have with this position.”

Early on, Jennings said, he was under pressure to spend money on costly infrastructure projects. Chief among those was separating sewer and stormwater pipes to prevent raw sewage from flowing into Casco Bay during heavy rainstorms. The city had been under a consent decree since 1991 to comply with the federal Clean Water Act, but had failed to take action. And the U.S. Environmental Protection Agency, he said, was threatening to refer the matter to the U.S. Department of Justice.

Since then, the city has spent more than $100 million on these projects.

“Unfortunately, it’s stuff that goes underground that no one really knows about,” Jennings said of the EPA work. “But it’s incredibly important for Casco Bay and the overall health and well-being of  the city.”


He also successfully advocated for additional funding – $15 million over three years – to upgrade the city’s “embarrassing and dangerous” fleet of vehicles and equipment, which included unheated plow trucks.

Jennings strategized with advocates for the working waterfront in 2019 to avoid a citywide referendum over a proposal to build a waterfront hotel. He convened a group of waterfront stakeholders and adopted policies to prevent the hotel project – which would have increased traffic on Commercial Street and put more pressure on fishermen. He was chipping away at a plan to address Commercial Street’s traffic, including an autonomous shuttle service, but it was derailed by the pandemic.

Ironically, Jennings said his new city of Clearwater is preparing to pilot an autonomous shuttle service along its waterfront.

Jennings noted that during his tenure Portland has successfully diversified its economy so it’s not as reliant on tourism. In recent years, the city has landed corporate headquarters for Wex and Sun Life U.S. And it is now home to the fledgling Roux Institute at Northeastern University, a graduate school and research center working with local companies on cutting-edge technology that include artificial intelligence, advanced life science and medicine, and computer and data sciences.

The city also made strides in environmental sustainability, building a solar array on an old landfill on Ocean Avenue, introducing more electric vehicles to the city fleet and adding charging stations around the city.

In discussing his accomplishments, however, Jennings was adamant about sharing credit with the city staff, to whom he gave more professional development opportunities.


“I say ‘we’ specifically because if not for the best group of people I’ve ever had the honor to work with, meaning a city staff, none of this would have been accomplished,” Jennings said.


Portland’s citizenry is very politically engaged, however, and increasingly expects more than basic services from city officials. Organizations with statewide goals often look to pass progressive policies first in Portland in hopes they will catch on. The city has dozens of neighborhood organizations and friends groups, many with highly focused agendas.

City officials often get accused of not listening to residents who are interested in certain policies or projects, but that’s not the case, Jennings said. He said the city listens to comments at public meetings and reads through emails. But his role has been to prioritize city spending and staff attention.

“We got back to the basics,” Jennings said. “What the frustration is is that it’s a city of 68,000 people and the belief is the city should solve every problem. We’re supposed to be like San Francisco; Portland, Oregon; or Seattle; when you have a limited budget and you’re simply trying to get sidewalks fixed.”

Jennings was not shy about using his annual budgets to force conversations about controversial topics, including ending the city’s longstanding yet unwritten policy of providing shelter to anyone in need in 2019; ending direct medical services provided at the India Street Clinic in 2016; ending local financial aid for undocumented immigrants in 2019.


Looking back, Jennings said he regrets just one thing – his ill-fated attempt to remove a brick bearing his name from a memorial honoring fallen firefighters in 2019. As founder and general manager of the Maine Red Claws, Jennings had spearheaded efforts to raise more than $20,000 to build the memorial. But he ordered that the brick be removed after the firefighter union waged an unsuccessful public campaign against decommissioning a fire engine on Munjoy Hill. Jennings thought the union was stoking fears in the community about a proposal made by the fire chief.

“I reacted in a very emotional way, so I definitely regret doing that,” he said. “I have a lot of affection for the members of the Portland Fire Department – not necessarily the union leadership at times, but that’s just the nature of the job.”


Jennings clashed regularly with former Mayor Ethan Strimling, who accused the city manager of not providing him with enough access to city staff because of their ideological differences. Jennings disputes that charge and says that he accommodated Strimling’s repeated requests for in-person staff briefings. But Strimling was only one vote on the council, he said, and his priorities did not often align with the council’s collective goals.

Portland City Manager Jon Jennings looks away from Mayor Ethan Strimling as he speaks during a contentious workshop in 2017 on the role of an elected mayor. Carl D. Walsh/Staff Photographer

Public records revealed the internal debate over staff access and mayoral power. But a remarkable public meeting in July 2017 laid bare the raw tensions inside City Hall, with Jennings and Strimling trading accusations. It ended with Jennings saying he would rather resign than allow Strimling unfettered access to city staff. The council at the time stood behind Jennings.

“In terms of Strimling, that was the worst experience of my professional life,” Jennings said. “I’m happy to go on record saying that. I have been around a lot of people in professional basketball and the White House, you name it. I have never been around anyone quite like him.”


Strimling said Friday in an email that he still believes Jennings was trying to thwart his policies by limiting his access to city staff. He said he is pleased the charter commission is considering structural changes to grant more power to elected officials.

“It’s disappointing that Jon continues personal attacks, even as he exits our city,” he said. “In terms of Jon saying our interactions were the worst experience of his professional life, the feeling is mutual.”

Mayor Kate Snyder, who was elected in 2019, said Friday that she has not encountered any issues working with Jennings and she understands the need to prioritize elected officials’ requests of city staff, who have myriad daily responsibilities.

It’s not as restrictive as maybe it’s been made out to be,” Snyder said. “It’s a matter of asking him to be the point person on (staff) meetings.”

Snyder said she has disagreed with Jennings on things like the need to put general fund money into bike lanes and public transportation, but she’s still been able to work with him and get information from staff.

“I don’t think it has anything to do with ideology,” she said. “There have been times we have been in absolute disagreement, but it hasn’t prevented us from working together.”



Black Lives Matter Portland targeted Jennings personally during protests in the summer of 2020 calling for racial justice. The group, now called Black POWER, wanted the council to fire Jennings because they said his policies “hurt poor, predominantly Black and brown people.” They accused him of criminalizing poverty, cheerleading gentrification, abandoning immigrants, attacking essential health services, silencing free speech, denying humane housing and opposing school funding.

At the time, councilors called a news conference to affirm their support for the manager.

Black POWER did not respond Monday to a request for comment about Jennings’s departure and whether their 2020 concerns about him are still relevant.

The outgoing city manager said he felt the work he did was sometimes mischaracterized. While the city has cracked down on criminal behavior in Bayside, which is home to several shelters and social services, Jennings, whose single mother worked in a factory and relied on government assistance, disputes that the aim has been to target people who are homeless or poor and in need of help. He said the real aim has been to protect the most vulnerable from those who would prey on them.

“I find it offensive to the homeless when all of these folks are lumped together, because I believe that people who are in a state of emergency homelessness deserve our compassion and understanding and help,” he said. “But there’s this whole other group of people that are simply here to create chaos.”


Jennings worked with the council to lay the groundwork to replace the aging and bare-bones Oxford Street Shelter with a new homeless services center in Riverton. The new facility, which has been approved by the planning board but could be derailed by a citizen referendum, would have beds, a medical clinic, day space, a soup kitchen and wraparound services. It was a continuation of the work he began in 2011 as part of a task force looking to end and prevent homelessness.


Jennings proposed eliminating the Portland Community Support Fund, which was created in 2015 to continue providing financial assistance to asylum seekers who were expected to lose state benefits. Those state cuts, however, never happened, because Republican Gov. Paul LePage would not veto a bill that preserved that assistance. And the council voted in 2019 to keep the local fund since it still was providing assistance to people not eligible for the state’s General Assistance program.

As few months later, Jennings led the city’s response to an unexpected influx of asylum seekers from the southern border.

Jennings declared a citywide emergency, allowing him to leverage state resources and convert the Portland Expo into a temporary shelter for hundreds of migrant families who came to Portland after they crossed the southern border. That summer, the city partnered with community organizations, local businesses and social service agencies to feed, shelter and house the migrants.

BLM Portland also criticized Jennings for continuing to use the Expo, even though dorm rooms were being offered at the University of Southern Maine campus in Gorham. The city’s decision stemmed from the fact that the dorms would be a short-term solution and disruptive to efforts to find long-term housing for the families. And the Expo was available for longer than the student dorms were.

Jennings received an award from the Maine Town and City Managers Association for his leadership on the asylum issue.

He saw the community response as a template for what can be accomplished when everyone comes together around a common goal.

“That’s when you’re most proud in this job,” he said. “In many ways, I wish we could just get back to where everyone wants to work together for the common good, as opposed to tearing each other down because they don’t agree with you.”

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