City Manager Jon Jennings.in September of 2018 at a City Meeting, in Portland.

Jon Jennings, former city manager of Portland, is expected to be fired next month from his newish position in Clearwater, Florida according to a recent article in the “Tampa Bay Times.” On Thursday evening, city councilors in that city were expected to vote on a salary increase for Jennings.

But the agenda quickly pivoted when councilors expressed disappointment in his poor communication skills – something that he was well known for in his position in Portland as well.  In a recent profile of interim city manager West in the “Portland Phoenix,” West acknowledged that Jennings’  communication skills were not highly developed.  West, an attorney, served as head of the city’s legal department during the Jennings’ administration.  Who knew?

A vote of 3 – 2 supporting his dismissal was short of the super majority required in this instance.  So, another vote for his dismissal has been scheduled for January 5, 2023.  According to the same newspaper article, Clearwater Mayor Frank Hibbard said, “But I am of the opinion that we need to move on.”  Clearwater has a population of just over 100,000 people and Jennings said he had visited the area in the past.

One of his legacies in Portland was his ongoing power struggle with then Portland  Mayor Ethan Strimling.  It became so intense that it even broke out in city council chambers in 2017.  Jennings allegedly said that he considered resigning at that time as well.

More recently, Jennings came under fire in Portland for setting city policy with no accountabiity at the ballot box.  Rather, the city council just acted as a rubber stamp for his policies set in place.  That was one incentive for the establishment of a city charter commission that would have more clearly defined the city manager’s job as strictly operational and not a policy setter.  The latter to be the responsibility of the elected and not appointed mayor.  However, the proposal failed at the ballot box last month.

Prior to his tenure as city manager in Portland, Jennings served as assistant city manager in South Portland.  He sometimes visited the Maine Mall there presumably to check on a drink concession he owned there.  This blogger had several casual conversations with Jennings there in which he chatted about his background as a manager for the Boston Celtics and his work with the Maine Red Claws.  Jennings was an early partner with Chris Thompson in the deveopment of Thompson’s Point.   He made multiple appearances at city hall in pursuit of that project.  However, he left that venture because he didn’t like the “direction in which it was headed.”  So he sold his share of the project to a friend, he told this blogger. Prior to this he also worked in the Clinton White House he said.  Jennings is an attorney.

For more background information on the rift between Jon Jennings and former Mayor Ethan Strimling, please visit two posts herein dated July 31, 2017.