Former Portland city manager Jon Jennings was fired Thursday from his current job as city manager in Clearwater, Florida, after city councilors there expressed concerns about his performance and said he wasn’t “a good fit.”

The council voted 3-2 to dismiss Jennings a little over a year after they first hired him.

“I really think this is about fit and I don’t think Mr. Jennings is a good fit for this city,” Mayor Frank Hibbard said.

Former Portland City Manager Jon Jennings Brianna Soukup/Staff Photographer

Hibbard and fellow councilors talked at length about the reasons for their decision during a public meeting that was streamed live online. It was unclear whether Jennings was present at the meeting and he did not respond to messages left on his cellphone or an email Thursday seeking an interview about the council’s decision.

The three who voted to fire Jennings noted issues with communication and a lack of willingness to accept their feedback and make improvements.


Hibbard provided several examples of the issues he had with Jennings. In one example, Hibbard said the city had scheduled strategic planning meetings to be held at four locations that would also include an update on American Rescue Plan Act funding.

A few hours before the first meeting, Hibbard said Jennings called him and asked if Hibbard would be leading the sessions. “I said, ‘I beg your pardon? No one has asked me to facilitate that,'” Hibbard said. “I said, ‘Why hasn’t staff been working on a process that we’re going to present to our citizens?'”

Hibbard said he worked with staff to throw together a makeshift presentation. The same night he found out the ARPA information had been altered from what he had seen in one-on-one meetings with Jennings.

In another example, Hibbard said that $2.1 million was authorized for an amphitheater sound system without council approval. “That is beyond any staff member’s ability to spend money,” Hibbard said. “I asked him specifically how that was approved and he couldn’t give me an answer. … I still don’t have an answer to this day.”

City councilors in Clearwater, Florida, debate whether to fire Jon Jennings during a special meeting that was live streamed Thursday night.

Hibbard said he did several reviews with Jennings, who did not agree with some of the mayor’s assessments. “He said to me, ‘This won’t be a one-way conversation,'” Hibbard said. “I said, ‘What do you mean by that?’ and he said, ‘I’m going to push back on some of the things that you don’t think I’m doing well.’ I said, ‘That’s your prerogative but this is not a peer review. These are your five bosses.'”

In December, after the council took an initial vote to terminate Jennings, Hibbard said he sent Jennings an email telling him the action wasn’t personal and requesting that Jennings communicate with assistant city managers about any issues he had been working on that they weren’t aware of.


“We have heard crickets since that time and that was three weeks ago,” Hibbard said. He said Jennings will receive 20 weeks of severance pay.

Councilors Kathleen Beckman and Lina Teixeira echoed Hibbard’s concerns. In numerous instances, Beckman said she frequently felt like she “wasn’t getting straight or complete answers on critical questions and agenda items.”

Beckman said her breaking point came during council consideration of a multimillion contract for management of the 4,000-seat amphitheater under construction. “Information was incomplete, communicated extremely late in the process and only provided when I requested the information in writing,” Beckman said.


The two councilors who voted against firing Jennings said they were aware of issues that needed to be addressed but felt that could be done while retaining Jennings as city manager.

“None of these things were brought up at the annual review,” Councilor Mark Bunker said. “It seems to me that would have been an appropriate time to say, ‘Listen, there are some issues we need to address.’ Instead, we had a review that said, ‘You did a good job. There were some things we argued about, but it was a perfectly acceptable year,’ and then boom.”


Councilor David Allbritton said he appreciated Jennings’ approach to the job and that it wasn’t without challenges. “He really had to delve into a lot of the departments and straighten things up, which he did, and I think he got a lot of respect from employees for doing that,” Allbritton said, noting Jennings’ creation of the city’s first public works department as a success.

But Allbritton also noted Jennings’ health as a concern, saying Jennings contracted COVID-19 three months into his tenure and that it set him back. “He was in a fog for a long time, while he was doing all this stuff. … We could see he wasn’t all there,” Allbritton said.

More than a dozen people submitted public comment, either written or in-person, to the council before its decision, with most people speaking up in support of Jennings.

Resident Jonathan Wade, who interacted with Jennings one-on-one while he was running for the council, said Jennings seemed genuine and eager to work with the neighborhoods of the city.

“I think starting the process over with a search will take a bit of time while there are many tasks before the community,” Wade said. “We’re struggling to keep a Martin Luther King center. That’s an issue that’s ongoing. We need someone who is proactive to all the city, and Mr. Jennings has shown himself to be that.”



Jennings was hired as Clearwater city manager in September 2021 after serving six years in Portland, where he 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 and ending direct medical services provided at the India Street Clinic in 2016.

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.

Portland has yet to name a permanent replacement to fill Jennings’ role. Danielle West, who previously served as the city’s corporation counsel, has been holding the job on an interim basis since November 2021.

The Portland City Council recently resumed its search for a permanent city manager after a city-wide referendum proposing major changes to the structure of the mayor and city manager jobs put the process on hold. The question was defeated in the November election and the city is expected to start advertising for the job later this month.

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