Portland City Manager Jon Jennings would start work as city manager in Clearwater, Florida, on Nov. 8 and earn an annual salary of $230,000, according to a contract that will be voted on next week.

That timeline, however, would not allow Jennings, who was selected by the Clearwater City Council last week, to honor a 90-day minimum notice to terminate his contract in Portland.

Jon Jennings speaks to the Portland City Council after members voted in favor of approving him for city manager post. Derek Davis/Staff Photographer

Mayor Kate Snyder said she discussed the issue with Jennings this week and he indicated that, if his contract is approved, his last day in Portland would likely be Nov. 1.

Since that doesn’t meet the 90-day requirement, Jennings may not be eligible for certain end-of-employment compensation, she said. It also means the city will have to move more quickly to find an interim manager, a process that is scheduled for a workshop next Thursday.

Snyder understands Clearwater’s urgency in hiring a new manager, since their previous manager passed away.

“Of course, I had hoped for the 90 days, but it is what it is,” she said. “We’ve got to get an interim city manager in sooner rather than later, ideally with some overlap with Jon.”

Portland recently hired Anne McGuire as assistant city manager, but she is new to the city, having previously worked in New York. McGuire, who has known Jennings since the 1990s when she was a special presidential assistant for cabinet affairs under President Bill Clinton and Jennings was a White House fellow, started her new job on Aug. 30.

Meanwhile, the Tampa Bay Times reported Thursday that Jennings will join several Clearwater councilors this weekend when they visit Pennsylvania to network with the Philadelphia Phillies, who have a minor league baseball team and spring training facility in Clearwater. Jennings helped to bring the Maine Red Claws – now the Maine Celtics – basketball team to Portland before becoming city manager.

Snyder said she expects Jennings will be taking some personal days over the coming weeks to look for housing (his proposed contract says Clearwater will pay up to $35,000 in moving costs) and to get up to speed on issues that he will be dealing with in Florida. But she’s confident Jennings will remain focused on Portland.

“I also feel very assured he will stay on full time in Portland through Nov. 1,” she said. 

Jennings did not respond to questions about his proposed end date and reported trip to Philadelphia this weekend, but a City Hall spokesperson replied on his behalf.

“While he is meeting in (Philadelphia) during his weekend time, Jon would like people to know that he was raised to finish any job he takes on and he will be supremely focused on completing all the important work that is left to be done before he leaves,” Jessica Grondin said. “He is passionate about this city and will miss it and the people he has worked with. No one should doubt his commitment to the work at hand. He has worked around the clock for the last six years and will continue to do so until his last hour on the job.”

Jennings has been city manager in Portland since 2015. Last year, he earned a salary of $179,790, 28 percent less than his new projected earnings.

Clearwater is a city of about about 115,000 residents located in the Tampa Bay region. The city government is run by the city manager, who reports to an elected mayor and four-member city council. It has an annual budget of $615 million, including nearly $165 million in general fund expenses, and nearly 1,850 full-time employees.

Portland, meanwhile, has about 66,600 people and an elected mayor who is part of the nine-member council. The city has a $268 million budget, including $212 million in general funding spending, and employs more than 1,400 people.

City councilors held a workshop on Aug. 30 to discuss the search for a new manager. The session was scheduled before Jennings was named as a finalist for the Clearwater post, but his contract is set to expire in July 2022 and he already had indicated he would not seek a renewal.

During the August workshop, councilors agreed that the city would need to name an interim manager if Jennings got a new job. But they were split about whether the city also should seek a permanent replacement, given the uncertainty associated with the ongoing charter review, which is expected to include an examination of the city manager’s role. A majority of the elected charter commission members already have expressed support for demoting the position and giving more power to the elected mayor.

Snyder said the council could vote on an interim manager sometime in October.

“I think we have to act sooner rather than later,” she said.


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