Portland City Manager Jon Jennings is a finalist for a similar post in Clearwater, Florida.

The Clearwater City Council announced Thursday that Jennings is one of four finalists in its search for a new manager, according to the Tampa Bay Times. He was one of 109 people to apply for the post to manage the city of 115,000 people just west of Tampa. Interviews with finalists will be conducted on Sept. 1 and 2, the newspaper reported.

Jennings said in a written statement that, as of now, he is seeking only the position in Clearwater.

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

“It has been an honor to serve as city manager in Portland for the last six years. To work with a very talented and committed staff has been a dream. I’m proud of all we have accomplished together,” he said. “It has always been my intent to leave after this year. When the opportunity to apply for the same position in Clearwater became available, I knew I wanted to apply. I’ve been fortunate to visit Clearwater over the years and found it a wonderful city. I am not applying for any other positions at this time as I believe the opportunity in Clearwater is perfect for me if I am selected.”

Jennings was named Portland’s city manager in 2015. His contract was extended for a year in November. At the time, Jennings said he “agreed to stay on” to help the city continue managing its response to the coronavirus pandemic. The contract expires in July 2022.

His potential departure comes as residents consider making major changes to city government, including whether the city of roughly 66,600 people should be run by a professional manager or an elected mayor.


Mayor Kate Snyder said the council has scheduled an Aug. 30 workshop to discuss how it plans to fill the position. She said if Jennings is selected for the Clearwater post, he will likely give 90 days notice to the city, forcing councilors to select an interim manager to oversee daily operations. The council would have to decide whether that interim manager should serve until the charter review is complete, or seek a permanent manager, she said.

“I have been very open-minded about which is the right pathway,” Snyder said. “You can logically argue both ways.”

The council’s search for a permanent manager would almost certainly be complicated by the ongoing review of the city charter – the city’s founding document that lays out the basic structure and lines of authority of city government.

A majority of nine elected charter commissioners campaigned on granting more power to the elected mayor, who serves a four-year term and earns a full-time salary but has no executive authority. Those candidates also called for demoting the manager position to an administrative assistant serving under the mayor or eliminating the position entirely.

About 15 of the roughly 220 Maine municipalities with managers are currently looking to fill that position, according to the Maine Municipal Association. One of those communities includes the city of Bangor, whose longtime manager, Cathy Conlow, stepped down to become executive director of the MMA.

“I do want to be respectful of the fact the community is having this (charter) conversation,” Snyder said. “Until a recommendation is made and voted on, we’re not going to know the will of the people.”

Jennings came to the city at the same time the city was implementing the new elected mayor position. His tenure overlapped with all three mayors elected since 2011. After a serving a few months with Michael Brennan, Jennings had a series of high-profile clashes with Mayor Ethan Striming over the powers and jurisdiction of the mayor’s position, with a majority of councilors siding with the manager. His relationship with the current mayor, Snyder, appears to be much smoother.


Snyder said she has a good working relationship with Jennings.

“One thing that I learned during the tenure of the last mayor and during the campaign is it’s important to be mindful of the roles as they have been defined in the charter,” she said. “We will sometimes remind one another that ‘that’s your lane’ and ‘that’s my lane,’ and there has been a lesson learned on that front.”

Since clashing with Strimling, Jennings has come under fire from progressive activists, who accuse him embracing gentrification and not doing enough to address the needs of people experiencing homelessness and other marginalized communities. Black POWER, the group formally known as Black Lives Matter, called on the city to fire Jennings last summer as part of its calls for racial justice. But several councilors responded with a news conference to express their support for Jennings.

He has advocated for the city to embrace so-called smart city technology and to carve out an identity as an innovation hub. And he has been working with councilors on a plan to build a new 200-bed homeless services center in Riverside, a proposal opposed by residents, who are seeking a referendum to block it.

In recent years, he has overseen the city’s response to two emergencies – the ongoing coronavirus pandemic and the unexpected arrival of hundreds of migrants seeking asylum in 2019.

Jennings received a leadership award from the Maine Town and City Managers Association for the city’s response to the arrival of 450 asylum-seekers. The city opened a shelter at the Portland Expo, collected nearly $1 million in donations, and worked with area agencies and governments to find housing for the families.

Jennings’ salary in 2020 was $179,790.

The Tampa Bay Times reported that the other finalists for the Clearwater position are: Milton Dohoney Jr., former assistant city manager of Phoenix, Arizona; Alfred Fletcher, assistant chief administrative officer of Montgomery County, Maryland; and Keith Moffett, county manager for Macon-Bibb County, Georgia.

Only subscribers are eligible to post comments. Please subscribe or to participate in the conversation. 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.

filed under: