Pious Ali and governance committee screenshot
City Councilor Pious Ali, bottom row, described a contentious working relationship with former City Manager Jon Jennings for the Charter Commission governance committee on Monday. He said Jennings was a "good politician" who pushed his own agenda and prevented the council from meeting with staff. (Portland Phoenix/Colin Ellis)
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Current and former Portland city councilors on Monday criticized former City Manager Jon Jennings as vindictive and manipulative.

They also said the office of the mayor is too weak to be truly effective.

Meeting remotely with the Charter Commission’s governance committee, Councilors Pious Ali and Belinda Ray, and former Councilors Kim Cook and David Marshall described how policies are developed and the working relationships they had with various mayors and managers.

Jon Jennings
Former Portland City Manager Jon Jennings.

Ali and Cook had the harshest criticism for Jennings, who left the city on Nov. 1 to become the manager in Clearwater, Florida.

Cook, who left the council voluntarily in 2020 after serving one term, said she had a poor relationship with Jennings and he did not support policies she was interested in pursuing.

“Trying to push big policy is extremely difficult if you’re not in the good graces of our now former city manager,” Cook said.

Cook said while councilors met regularly with Jennings, she eventually stopped having meetings or conversations with him in the spring of 2019. She said she wanted the city to have a committee dedicated to the first phase of its Recode revaluation project, which Jennings strongly disagreed with.

“The manager plainly told me that I may have won the battle but I wasn’t going to win the war,” Cook said. “I felt threatened and really didn’t trust meeting with him very often, alone at least. Our meetings became very infrequent.”

Ali said Jennings was savvy enough to know he had to keep at least five councilors happy at all times because five councilors are needed to approve motions. But Ali, along with Marshall, said the city has a strong manager, weak council, and weak mayor, and unless that is changed, “I cannot see councilors and mayors implementing the agenda that they ran on.”

He described a situation before the coronavirus pandemic where he advocated for new public restrooms to be installed throughout the city to better serve the homeless community. Jennings said he would not support the idea, but the same proposal was later made by a different councilor, and “suddenly it was the best idea brought forward.”

“Probably the manager agreed more with them than with me,” Ali said.

Ray, who is retiring from the council, said she had a slightly different experience: she often “butted heads” with Jennings, she said, but he would acquiesce to the will of the council if the votes dictated it.

“He was a strong-willed person, but he had nine bosses,” she said.

Ray said Jennings didn’t set city policy beyond drafting the first version of the municipal budget. Other councilors, however, have said he did, and that the charter allows a strong manager to do so.

Marshall said previous managers took similar approaches to policy goals. Mark Rees, he said, tried to sell a portion of Congress Square Park during his tenure. His approach led to political problems, Marshall said, when the sale of a portion of that public space was ultimately supported by the City Council and Mayor Michael Brennan in 2013 but was defeated by a citizen referendum.

Ali, Cook, and Marshall said citizen initiatives are now the approach the public is taking to respond to policies coming from City Hall.

“I see it as crossing the line when a manager pushes ideas,” Marshall said. “If I had been on the council I would have had strong feelings to his approach.”

Ali and Cook also described scenarios where Jennings prohibited councilors from speaking directly with city staff or department heads.

“The manager may have to answer to nine councilors,” Ali said. “(But) Jon did build a strong firewall between councilors and staff.”

All requests for staff guidance had to go through Jennings, which Ali said could be problematic. For example, if Jennings disagreed with the initiative a councilor was pursuing, he said staff could be told not to provide the best information or guidance.

Ali, who said he had a close relationship with former Mayor Ethan Strimling when Strimling and Jennings clashed publicly over the power dynamic, said he stopped meeting with the former mayor as often when that clash intensified.

He said it remained clear that he and Jennings did not see eye-to-eye on various policy initiatives. The former manager did not solicit him to vote certain ways, Ali said, probably because of their different opinions.

“Even though the last manager was not supposed to make policy, he was a good politician,” Ali said. “The previous mayor became like the bogeyman.”

Several of the councilors said the existing mayoral position is relatively weak, because the person who holds that position is just another councilor, with one of nine votes on the council.

Ray said Mayor Kate Snyder has excelled as a facilitator who understands she isn’t strong enough to push policy on her own: she needs to build coalitions and ensure they have at least five votes, which is the same as any other councilor. But she said if a mayor puts in the time to build relationships with the council, the manager, other mayors, and lawmakers in Augusta, it can be a powerful role.

On the other hand, she said, Strimling tried to promote policies on his own.

Marshall said the mayor is weak as a result of compromise by the last Charter Commission. He said the mayor lacks executive power and is a difficult position for candidates who run on a platform because they need five council votes to get anything done.

Marshall, who only served under Brennan, said he was more of a mediator.

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