Jennings to leave job as Portland city manager in 2022

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City Manager Jon Jennings, who became a lightning rod this summer for activists who claim the city isn’t doing enough to root out systemic racism, will step down in 2022.

His decision was announced following two recent private performance review sessions with the City Council – the first review Jennings has had in three years.

Jennings, 58, was hired in July 2015, after previously serving as the assistant city manager in South Portland. His contract was renewed in 2017 and was set to expire in July 2021. His annual salary is nearly $170,000; he was originally hired at a salary of just over $148,000.

The council Monday night conducted its first reading of his proposed contract extension through July 12, 2022, and will vote to approve it Nov. 9.

Portland City Manager Jon Jennings

According to a City Hall press release, Jennings told councilors during his review that he would consider a one-year extension, but not another three-year renewal.

“In light of everything the city is facing right now due to the pandemic and its impact on our fiscal health, I agreed to stay on for an additional year to assist the Mayor and Council as we continue to navigate these unprecedented times,” Jennings said in the release.

According to the memo to the council for the first reading of his extension, Jennings could serve an additional three months after this extension if the city has not hired a replacement. He would be eligible for a bonus of more than  $21,000 within 45 days of his contract’s conclusion.

Jennings has had a turbulent last few years on the job, and the position he holds could end up changing significantly depending on recommendations from the upcoming Charter Commission.

The commission, which was approved by Portland voters in July and will be elected and start work next year, was partly the result of voters’ concerns about the murky separation of powers between the city manager and the elected mayor. Jennings, who is hired by the City Council, is in charge of administration, while the elected mayor leads the policy-making council.

The last Charter Commission, convened about a decade ago, decided to overhaul the system. Previously, the mayor was a ceremonial position appointed by the council.

Opponents of Jennings have said his office is too powerful and unaccountable. He publicly clashed with former Mayor Ethan Strimling, who advocated during his term for a power shift towards an accountable elected mayor. 

Strimling, the city’s second popularly elected mayor since 2011, wanted his position to have more power over city policy. Strimling and Jennings had several high-profile disagreements, including the closing of the India Street Public Health Center and the city budget in 2016. The clinic did ultimately close, although its services were transferred to another facility. Strimling lost his re-election bid in 2019 after continued disagreements with the council.

Jennings came under fire this summer when protesters called for his resignation during several events by Black POWER, formerly known as Black Lives Matter. During those events, some people called on Jennings to step down, accusing him of creating policies that negatively impacted poor people and people of color. Several city officials, including Mayor Kate Snyder, defended Jennings.

“The Council and I are grateful for Jon’s leadership and steadfast commitment to the City of Portland,” Snyder said last Friday in a press release. “I look forward to continuing our work together as we respond to the myriad of challenges and opportunities.”

In his statement last week, Jennings said it has been an honor to serve the council and city.

“We’ve made great strides toward streamlining our processes, improving customer service, and ensuring our most vulnerable citizens are cared for,” he said. “But there is more work to be done, and that’s why I look forward to the opportunity to continue serving as Manager for a little while longer.”

Jennings is known also for helping to bring professional basketball to Portland, as a founder and first president of the Maine Red Claws, where in 2010 he was named the NBA D League Executive of the Year. He previously spent 11 years with the Boston Celtics as a scout, assistant coach, and director of basketball development.

He holds a master’s degree in public administration from Harvard University, and has also been a senior assistant in the White House Office, ran unsuccessfully for the U.S. House of Representatives in Indiana in 2004, and directed the Massachusetts offices of former U.S. Sen. John Kerry.