Jon Jennings speaks to the Portland City Council. Derek Davis/Staff Photographer, file

Former Portland City Manager Jon Jennings, who left Maine to take a similar job in Clearwater, Florida, appears to be on his way to being ousted from that job, the Tampa Bay Times reported.

The Clearwater City Council voted 3-2 Thursday to begin the process of firing Jennings. Because the council’s initial vote was not a supermajority, it would take a second vote to dismiss him, according to the Times. A special council meeting is scheduled for Jan. 5 to consider Jennings’ status.

Jennings was Portland’s city manager for six years and had previously spent two years as assistant city manager in South Portland. He also worked in professional sports, both as an assistant coach for the Boston Celtics and founder and general manager of the Maine Red Claws.

Jennings left Portland in November 2021 and took over as city manager in Clearwater later that month. He has been there for slightly more than a year.

The move to fire Jennings came as the Clearwater City Council was considering giving him a raise, according to the Times. Some councilors complained about his communication style and said he was slow to prepare them for a major vote over management of a 4,000-seat amphitheater.

Clearwater Mayor Frank Hibbard recently said he had informed Jennings that he felt he was the wrong fit for the city. Hibbard declined to divulge a list of concerns he had provided to Jennings about his performance, the Times reported. Emails to several Clearwater councilors were not answered Saturday.


Jennings decided in June 2021 to leave the Portland job after voters elected a charter commission to consider changes to the city’s form of government.

Among the changes considered by the commission was to create a stronger, executive mayor and replace the city manager job with a new chief operating officer who would report directly to the mayor. One commissioner wrote in a social media post at the time that Jennings would be “the last white supremacist city manager.”

Jennings was offended by that. He told the Press Herald at the time that the comment upset his teenage daughter, who urged him to find another job.

During his Portland tenure, Jennings created the Team Harmony Foundation to bring young people together to stand against hate and bigotry and supported creating the city’s Office of Economic Opportunity to help new Mainers enter the workforce.

The move to replace the city manager position was defeated by city voters in November.

Jennings was hired as Clearwater city manager in September 2021. Councilors were impressed by Jennings’ “bulldog” demeanor in getting things done – the other candidates were more measured and less willing to take risks.


As city manager in Portland, Jennings oversaw the city budget process and managed a workforce of 1,400. He frequently praised city workers, oversaw a massive project to separate sewer and stormwater pipes to prevent raw sewage from flowing into Casco Bay during heavy rains and upgraded the city’s “embarrassing and dangerous” fleet of vehicles, which included unheated plow trucks.

Jennings saw increases in city budgets and property taxes as playing a role in the city’s overall affordability problems. He 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; and ending local financial aid for undocumented immigrants in 2019.

In an exit interview with the Press Herald, Jennings said his job was about governing. “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,” he said.

Jennings said he was frustrated with some who believed the city should “solve every problem” and that Portland, Maine, should be like Portland, Oregon; San Francisco; or Seattle. He said the city has a limited budget and needs to do the basics “like fixing sidewalks.”

Related Headlines

Only subscribers are eligible to post comments. Please subscribe or login first for digital access. Here’s why.

Use the form below to reset your password. When you've submitted your account email, we will send an email with a reset code.