The Portland Phoenix

Former manager Jennings fired from Florida post

The Clearwater, Fla. City Council fired city manager Jon Jennings Thursday night with a second 3-2 vote, citing concerns about his work dating back to April.

Jon Jennings
Former Portland City Manager Jon Jennings.

Jennings was city manager in Portland from 2015 to 2021, which was marked by an extensive public feud with former Mayor Ethan Strimling. After leaving Portland before his contract expired, he was hired to be the city manager of Clearwater just over a year ago.

At Thursday night’s special council meeting, Clearwater Mayor Frank Hibbard and Clearwater council members Kathleen Beckman and Lina Teixeira explained their reasons to call for Jennings’ termination. The process began on Dec. 15 when the initial plan to fire Jennings was proposed. Due to Clearwater’s city charter, the council needed a subsequent meeting weeks after the initial proposal to confirm the termination of Jennings’ contract since there were only three votes in support of the motion.

Screenshot of Clearwater Mayor Frank Hibbard at the special council meeting on Thursday, Jan. 5.

At Thursday’s meeting, Clearwater Mayor Hibbard shared several problems he observed with Jennings’ tenure, which he recorded in a notebook as early as April 11.

“[Jennings] was aware of the things I was not happy with,” Hibbard said. Many Clearwater residents sent in messages and spoke publicly at the meeting in defense of Jennings — primarily speaking in support of how he supported their neighborhoods in 2022 — but Hibbard reassured residents that it was warranted.

“This is not baseless,” he said. “I feel I owe it to the city to make a change.”

Hibbard highlighted failure to prepare the city’s strategic planning meetings on time. When Jennings told Hibbard, “I thought you were going to do it,” Hibbard said that he and staff had to throw a presentation together with only four hours before the meetings. The authorization of a $2.1 million amphitheater sound system, which Hibbard said was not approved by the council, was another concern.

“I still don’t have an answer [on how it was approved],” he said.

After an initial vote to fire Jennings in December, Mayor Hibbard said he contacted the city manager to tell him the decision wasn’t personal, and ask that he pass on any ongoing projects to the assistant city manager. He hasn’t heard anything from Jennings since.

Beckman and Teixeira maintained that their experiences working with Jennings were enough to warrant the change. Beckman explained that lack of communication reached a point where she was receiving “unclear answers on critical issues” from Jennings.

“Mr. Jennings is talented and has many good qualities,” said Beckman. “He is just not the right fit here in Clearwater.”

Council member David Albritton, one of two dissenting votes in the decision to fire the city manager, said that he felt Jennings’ “entrepreneurial” style of leadership could still be a good fit for Clearwater, and that there was still time to rectify previous mistakes.

Albritton noted that health had been an issue for Jennings, who reportedly contracted COVID-19 in January and being left “in a fog” for eight to nine months, according to Albritton.

“You could tell he wasn’t all there,” Albritton added.

Before he was Portland’s city manager, Jennings was assistant city manager for South Portland from 2013 to 2015. He was also a founder, president and general manager of the Maine Red Claws G-League basketball team and served in President Bill Clinton’s administration.



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