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Clearwater taps Portland, Maine, leader as first new city manager in 20 years

Jon Jennings will succeed city manager Bill Horne, who died Aug. 14, three weeks before retirement.
Jon Jennings, city manager of Portland, Maine, speaks on stage Wednesday during a question and answer session for the four finalists for Clearwater city manager at Ruth Eckerd Hall. The City Council gave Jennings the job on Thursday.
Jon Jennings, city manager of Portland, Maine, speaks on stage Wednesday during a question and answer session for the four finalists for Clearwater city manager at Ruth Eckerd Hall. The City Council gave Jennings the job on Thursday. [ LUIS SANTANA | Times ]
Published Sep. 2
Updated Sep. 2

CLEARWATER — The City Council voted Thursday to hire a new city manager for the first time in 20 years, unanimously selecting Jon Jennings, the top administrator from Portland, Maine, with a background in the federal government, the private sector and professional sports.

Council members pointed to Jennings’ entrepreneurial experience, as he raised $1.5 million to bring an NBA development team to Portland 14 years ago and recruited industry after becoming city manager in 2015.

They noted his “bulldog” demeanor in getting things done, which differed from the other three finalists who were more measured and risk-averse.

“The great thing is Clearwater isn’t broken, the next city manager is not walking into a mess,” Mayor Frank Hibbard said before the vote. “We have to answer the question: Do we want a caretaker, do we want a change agent?”

Council members praised all four finalists, who they got to know over two days of in-person interviews and a town hall forum. But they could see Jennings, 58, investing in Clearwater for the long term, although not expecting he’ll replicate the 20-year tenure of former City Manager Bill Horne, who died of a suspected heart attack on Aug. 14, three weeks before his planned retirement.

“I like his energy, I like his business experience, I like the idea that he’ll take risks and try new things,” council member Kathleen Beckman said of Jennings.

Portland, Maine, city manager Jon Jennings chats with Ruth Nickerson during a meet-and-greet event at Ruth Eckerd Hall on Wednesday, Sept. 1, 2021 in Clearwater.
Portland, Maine, city manager Jon Jennings chats with Ruth Nickerson during a meet-and-greet event at Ruth Eckerd Hall on Wednesday, Sept. 1, 2021 in Clearwater. [ LUIS SANTANA | Times ]

Jennings will come on during a pivotal time in Tampa Bay’s third-largest city. Officials are attempting transformational change for downtown with the $84 million Imagine Clearwater waterfront redevelopment, complicated by the presence of the Church of Scientology.

Leadership is working to better respond to sea level rise and climate change. Citizens are demanding attention for infrastructure projects, like improvements for the Drew Street east-west corridor.

This is also a period of significant change in leadership. Along with hiring the first new city manager in two decades, the council last week hired the first new city attorney in 27 years. David Margolis, chief assistant city attorney of Orlando, will succeed City Attorney Pam Akin next month when she retires after nearly three decades.

“I’m excited to work for the council and move Clearwater forward,” Jennings told the Tampa Bay Times. “It’s where I wanted to transition to, to further my career in municipal government.”

Jennings said his leadership style comes from his decade as a scout and coach for the Boston Celtics beginning in the late 1980s.

His interest in government prompted him to apply for a White House fellowship in 1997 with the Clinton Administration. He worked in the Office of Cabinet Affairs under Thurgood Marshall Jr. and as acting assistant attorney general for legislative affairs.

After an unsuccessful 2004 run for Congress as a Democrat in a red Indiana district, he raised $1.5 million to bring the Maine Red Claws, an NBA development team, to Portland.

He pivoted to local government, becoming assistant city manager of South Portland, Maine, in 2013 and city manager of Portland in 2015.

Jennings said he helped center an unstable government by accelerating stormwater and sewer upgrades and expanding training for department heads. He created a sustainability program and helped build a 4-acre solar farm. He oversaw what he called a progressive police department as it hired a substance abuse position to battle the opioid epidemic.

During the public interviews on Thursday, council members grilled Jennings about recent calls from progressive activists in Portland for him to resign. During protests for social justice last year, activists said he backed a “law enforcement approach to poverty, homelessness, and mental and behavioral health struggles,” according to the Portland Press Herald. The Portland mayor and City Council publicly defended Jennings’ commitment to racial and economic justice.

Jennings explained that as city manager he was the scapegoat for activists’ concerns that Portland’s government was created decades ago by a deal between the chamber of commerce and the Ku Klux Klan, a history he has not been able to verify.

“I’ve spent a lifetime of service,” Jennings said. “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,” he continued, referencing a Portland activist’s comment that he was a “white supremacist.”

He said the political climate in Portland became so toxic that his 17-year old daughter urged him to look for opportunities elsewhere.

Jennings described his desire to be a part of Clearwater, which he said is extremely well-managed but on the cusp of exciting change.

Jennings said his top priorities for Clearwater are establishing a working relationship with the Church of Scientology to help downtown revitalization, responding to the threat of climate change and deepening community engagement.

“It is an opportunity but it takes two sides to develop that kind of working relationship,” Jennings said of Scientology.

Council member Mark Bunker said he supported Jennings but had concerns about whether his bulldog nature may cause some stress Clearwater politics are not accustomed to.

Bunker noted a 2019 news story where Jennings asked that a brick bearing his name be removed from a firefighter memorial during tense negotiations between Portland and the fire union.

“I can see where he’s going to come in and he may be dynamic and he may do all the stuff we want him to do, but he also may cause a lot of stress,” Bunker said. “It may be worth it.”

Jennings noted his experience founding and running a nonprofit, the Team Harmony Foundation, dedicated to youth empowerment. He also discussed the gravity of climate change, referring to the issue as “a serious, serious set of circumstances we are facing.”

The other finalists were Milton Dohoney, former assistant city manager of Phoenix, Arizona; Charles Duggan, city manager of Redlands, California; and Keith Moffett, county manager for Macon-Bibb County, Georgia.