City Manager Jon Jennings won’t be on the ballot when Portlanders vote next month, but his presence looms over the election nevertheless.

Whoever is elected Portland’s mayor on Nov. 5 will be tasked with working closely with a man who has policy ideas of his own and who runs city operations and strictly controls access to city staff.

Jennings, who has run city government since 2015, has clashed repeatedly with incumbent Mayor Ethan Strimling, who was elected mayor that same year. Strimling has criticized Jennings’ policy of requiring all requests for information to be funneled through his office, rather than allowing councilors and the mayor to interact directly with staff.

Jennings makes no secret that he doesn’t get along with Strimling and would rather see someone else win the election. He even suggested that he would have to re-evaluate his future in the city if the incumbent is re-elected. But Jennings also says he will take the same approach as gatekeeper no matter who gets the job.

“I’ve had excellent working relationships with all of the councilors except the mayor,” Jennings said. “They all respect my position and that city staff does need to be protected from the political winds of the moment and provide their professional opinion in a safe environment.”

Jennings said the policy is necessary because he runs the daily operations of the city and staff can be easily consumed with responding to requests from the mayor or individual councilors. No other councilors have expressed concerns about his approach, which he said is common in strong city manager forms of government. And an outside legal opinion that was sought to clarify the mayor’s role explicitly endorsed Jennings’ communication policy as reasonable, given his responsibilities.

But Strimling said his questions sometimes go unanswered, making it more difficult to develop policies. Jennings and Strimling said they rarely meet and mostly communicate by email. Jennings said the mayor is rarely at City Hall these days. Strimling said that’s because City Hall is “a bubble,” so he spends his time out in the community.

Strimling said he can still be an effective mayor in a second term, even with a fractured relationship with Jennings.

“I would like there to be more of a partnership than currently exists, but we are where we are,” Strimling said. “It’s not about personalities, it’s about achieving results. Despite roadblocks being thrown up from a lot of sectors, we have gotten stuff done.”

The structure of the city’s government has some people questioning why the city needs a full-time mayor and a professional city manager. Strimling has said he’d like the city to move to a strong mayor system, like Boston or New York. But no one appears to be eager to reopen the city charter, which would be needed to change – or eliminate – either the manager’s or mayor’s position.

The current charter limits the power of the mayor as a policy leader and reserves operational control of the city for the manager. It envisions a collaborative relationship between the mayor and manager, who is hired by and reports to the entire nine-member council.  Jennings earned a salary of about $170,000 last year. The mayor currently earns $76,615 a year.


Strimling’s challengers say they would take a different approach to working with the city manager.

• City Councilor Spencer Thibodeau said he has never had any trouble getting information from staff, whether by sending Jennings an email, or asking questions of staff assigned to council committees.

“From my perspective, I have demonstrated that I can work within the framework Jon has set up,” he said. “I don’t see that as a barrier in any way to the success of the position. You get your questions answered at committee meetings and they get answered via email. It has not hindered my ability to represent my district and I don’t see how it could hinder me as mayor.”

Thibodeau said he’s been able to have those “tough conversations” with Jennings about policy differences, but has still been able to work collaboratively on other issues. As examples, he points to his vote against rezoning the western waterfront, restoring federal grants for Preble Street, his support of the four-school bond, funding to implement the pesticides ordinance and voting to increase funding for asylum seekers.

While Strimling does not believe the manager should be driving policy discussions for the council, Thibodeau believes the manager has a right to introduce policy proposals for the council to consider, especially through the budget process.

• Former School Board Chairwoman Kate Snyder said that, if elected, she would meet with Jennings to understand why that policy is in place. She said she’d follow the advice of her sisters, who once told her that when you take a new job, “the first thing you do is listen a lot. You don’t come in telling people who have been doing their job for years how to do their jobs.”

Snyder agreed that the manager, as well as other city staff, have a right to come to the council with their own policy ideas and that they need not all descend from the mayor’s office.

“I think that creates an environment of trust,” she said. “I’m not looking to overstep my authority.”

Travis Curran, a 33-year-old restaurant server, said he believes the city manager has too much power over city operations and seems to serve “corporate interests.” If elected, however, Curran said he would try to work closely with the manager.

His strategy is simple, he said: “By being as friendly as I can.”

Jennings said that if Strimling is re-elected, he would have to think about his future with the city, even though he loves the job, city staff and the city. He believes he’s operating within the boundaries of his job description and doesn’t plan to change.

“The last four years have been very difficult,” Jennings said, noting that he has about two years left on his contract. “The division that has been brought into City Hall and into city government is exactly like Washington, D.C.-style politics. And it is sad for me, because there are a lot of really good things we have done and do.”

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