Jon Jennings has been selected as the next city manager of Clearwater, Florida.

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

Jennings, who was named Portland’s city manager in 2015, was selected over three other finalists. His contract in Portland expires next summer but allows him to leave with 90 days’ notice.

Jennings said he is excited to begin negotiations with the Clearwater City Council, but suggested that it’s not yet a done deal.

“I am deeply honored the Clearwater City Council voted unanimously to support beginning negotiations with me to become the next city manager,” he said in a text message Thursday evening. “I am looking forward to negotiations with the city of Clearwater. It is an incredible opportunity for me. At the same time, I cannot help but be sad about possibly leaving Portland city staff, who are the best group of people I’ve ever worked with in my career.”

Mayor Kate Snyder said she spoke with Jennings on Thursday and has shared the news with the rest of the council.

“Jon has been offered the position, but has not yet accepted,” Snyder said. “If this is the right next step for Jon professionally and personally, I will wish him well and will work closely with him and the council to facilitate a smooth transition.


News of Clearwater’s selection was first reported Thursday by the Tampa Bay Times. The newspaper reported that the candidates were interviewed over the course of two days. The process included in-person meetings and a town hall event.

The newspaper reported that councilors were impressed by Jennings’ “bulldog” demeanor in getting things done, whereas the other candidates were more measured and less willing to take risks.

Jennings is poised to leave Portland as the city continues to respond to a surging COVID-19 pandemic and as the city is soliciting public input about how to spend the bulk of $46 million in federal funding meant to help cities and towns get through it.

It also comes as the Charter Commission is considering changes to the City Charter, essentially the city’s constitution, laying out the basic form of government. Among the issues to be discussed are the roles of the city manager and the popularly elected mayor, who serves full time but has no executive control.

A majority of the commission campaigned on strengthening the powers of the mayor and either demoting the manager to an administrator or eliminating the position altogether.

Any recommended changes would need to be approved by voters – possibly in November 2022.


The Portland City Council met this week to begin discussions about a city manager search. Portland is the largest municipality in the state. It currently has a $268 million budget, including $212 million in general funding spending, and employs more than 1,400 people. It’s also a regional service center and economic engine of the region and state.

Although councilors didn’t make any decisions Monday and plan to revisit the discussion in two weeks, a majority expressed support for beginning the search for a new permanent manager, rather than relying on an interim manager until fall 2022. But other councilors worried that uncertainty associated with the charter review could limit the pool of candidates.

Snyder said at the time that if Jennings provides 90 days’ notice and leaves early, the city would need to hire in interim manager. She said the council would meet again in two weeks to resume the discussion.

Jennings, who earned $179,790 in 2020, became Portland’s manager in 2015. He clashed with former Mayor Ethan Strimling over the limits of mayoral power, but has had a good working relationship with Snyder and the council through most of his tenure.

Jennings has been the target of progressive activists, including Black Lives Matters Portland, a group now called Portland POWER. Last summer, amid national calls for racial justice, BLM activists called on the council to fire Jennings, saying his policies harmed marginalized communities. The council, however, called a news conference and expressed support for Jennings.

In Clearwater, Jennings was questioned about being targeted by activists, including being called a “white supremacist” by a sitting charter commissioner, the Tampa Bay Times reported.

“I’ve spent a lifetime of service,” Jennings said in the Times report. “I have worked in the most diverse jobs and cultures in professional basketball, in business and in government.”

“It is frankly an outrageous, hateful statement that was made.”

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