Wheeler’s months are up, making some wonder, “What’s next?”

Part of being a politician is running for election, and most politicians will tell you that this is their least favorite part of the job. For Ted Wheeler, however, it has seemed at times that his least favorite part of the job is the job itself.

Wheeler has been Mayor of Portland since 2017, and before that served as State Treasurer from 2010-2017 and the Multnomah County Commissioner from 2007-2010. He was elected mayor in 2016 with almost 55% of the vote in an open primary.

About a year ago, Ted Wheeler made his displeasure with his job known when a reporter at The Oregonian heard him say, “I cannot wait for the next 24 months to be up," referring to the amount of time left in his term. However, this year, Wheeler has announced that he will run for re-election. If Wheeler is so displeased with his job, why is he running again?

City Commissioner Nick Fish offers an explanation. “Ted is human, and I don’t know what was going on in his head at the time, but every once in a while, we need to release some steam.”

“If you were to ask him now, I think he’d say ‘Yup, that was sort of a human moment,’” echoed Chet Orloff, a local historian and retired professor of Urban Studies and Planning at Portland State University and the University of Oregon.

Wheeler's “releasing of steam,” though, led some to believe that he may not seek re-election, especially after Portland’s string of one-term mayors. However, this past June, Wheeler began to make it known that he would seek a second term.

Wheeler understood that running for re-election would be difficult.

Being Mayor of Portland, “You're going to make enemies no matter what,” said Orloff, due to the fact that there is such a wide diversity of viewpoints and interests in the city.

Wheeler's quest for re-election, according to Fish, is driven by the fact that he feels he has unfinished business. Furthermore, breaking this trend would be good for the City of Portland, since it would give the people their first two-term mayor in quite a while.

Being a one-term mayor is somewhat of a Portland tradition. Portland has not had a two-term mayor since Vera Katz left office in 2005. The last three mayors, Tom Potter, Sam Adams, and Charlie Hales, each served a single term before exiting City Hall. Wheeler now seeks to change that trend.

However, there seems to be particular reasons that this slip happened. First of all, Portland’s system of government is particularly hard on the mayor, more so than other cities.

“In Portland, under our charter, the mayor actually has very limited authority. So, when you're the mayor, you essentially get blamed for everything. You have limited power, though, to actually fix things,” explained Fish.

“He’s in a very hard job. That's why three very talented predecessors before him only served one term… We’re probably the only city of our size with a commision-style of government,” said Fish.

Portland’s city government is structured, according to the City website, so that “the Mayor, four Commissioners and the Auditor are the City's six elected officials,” and “the Mayor and the Commissioners together make up the City Council.”

Fish has been in office since 2008 and called Wheeler “the most accessible mayor” he has ever worked with.

CatlinSpeak requested an interview with Mayor Wheeler about his campaign, but neither Wheeler nor his staffers returned calls and messages before this article’s publication.

Wheeler's last campaign was managed by Michael Cox, but Cox left the Mayor’s office in January of this year after disclosing a romantic relationship with a subordinate. This time around, the campaign will be managed by Jennifer Arguinzoni, another Wheeler staffer.

Wheeler is not facing much, if any, established opposition. If he receives 50% of the vote in the primary this spring, Wheeler will win the election outright. Receiving endorsements like Fish’s will help his cause.

“I think he has a compelling vision for our future, and I’d like to see him be able to continue that for another four years,” Fish said.

Wheeler’s campaign website touts his accomplishments, specifically regarding housing and the environment.

“I've served with four mayors. Three of them have been one-term mayors, which has been very disruptive for the city because you spend the first year ramping up, and if you don't run for re-election, your last year is a lame duck,” explained Fish.

Breaking up the flow of mayors hurts the city too. “Each mayor has had a different set of priorities, and frankly, it's been very challenging. I think serial one-term mayors are bad for our city,” said Fish.

Prior to Wheeler, Portland’s last three mayors were Tom Potter, Sam Adams, and Charlie Hales. Potter was the former Chief of Police, Adams was a former political staffer and City Commissioner, and Hales was also a former City Commissioner.

“Potter was a little bit over his head,” said Orloff. “He sort of had a vision of what he wanted for Portland, but he was never really able to articulate it. Plus, he came from the police department and he could have been a strong advocate for police reform, but he really didn’t tackle that.”

Orloff described the mayors before Potter, too.

“[Sam Adams] had the issue of a scandal at the beginning of his term, and I don't think he could ever overcome it,” Orloff said.

The mayor before Wheeler, though, Charlie Hales, seemed like maybe he could escape the curse of the one-term mayors. Orloff describes Hales as the “most sophisticated of the three [former mayors] and said “when Hales came into office, the tagline was ‘the adults have taken back City Hall.’”

“[Hales] wasn't able to build the kind of coalition that he wanted to. I also think he suffered, unfortunately, from the fact that the two previous mayors had been one-termers who had been weak mayors who didn't leave much of a legacy,” described Orloff.

Wheeler also has not inherited much of a legacy, but he has done the most with what he has: a city council that hasn’t always stood by him and an unhappy populous.

“The issue that Ted is going to focus on relentlessly now and then in his second term is a humane and compassionate understanding of homelessness,” Fish said.

According to Fish, Wheeler is not just doing this to win votes. “He's deeply committed to this work, and he's working very effectively with the [Multnomah] County Chair [Deborah Kafoury]. [Housing issues] will be the signature work that he continues to address in a second term.”

But what makes Wheeler different as a person than these past mayors? “For one, I think he’s smug,” said Orloff.

“Two, he’s more experienced in the political realm, both at the regional level and state level, so I think those things helped him. I think he's also mayor at a time when Portlanders are trying to grapple with where we’re going as a city,” said Orloff.

In Orloff’s view, Portlanders are “feeling a little bit lost, and it's a great opportunity for him to articulate what his vision for the city might be. If he’s able to do that, and then begin to build an administration around it for his second term, I think he will succeed.”

As for Wheeler’s electoral chances, Orloff said, “It remains to be seen if he will get reelected, but I think he will.”

Portland's mayoral primary is not until May 19 of next year.

The Portland City Council under Mayor Potter. Adams, then a City Commissioner, is seated second from the left. Image Courtesy of Pete Forsyth.

“He will have some challenges in his election,” predicted Orloff. “I think he needs to be very clear about what his vision for the city is, and how it’s different from the particular vision that people are attributing to his chief political adversaries right now.”

Of the people filed to run against him, the most formidable opponent is Sarah Iannarone, a community activist who Wheeler defeated in 2016.

According to a source who wished to remain anonymous and is familiar with the situation, a future gubernatorial or Senate bid for Wheeler is not at all out of the question.

“The only reason I think he might not is if he is so damaged or jaded from being Mayor of Portland,” the source said.

Wheeler has some experience on the statewide and national levels. Before becoming mayor, he was the state treasurer, and he has also been attacked multiple times by President Donald Trump throughout his term as mayor, especially for his policies regarding local protests.

“Portland is being watched very closely. Hopefully the Mayor will be able to properly do his job!” the President tweeted at the time of the notorious ANTIFA-Proud Boys clashes on Aug. 17 of this year.

Because of issues like these demonstrations, Orloff thinks that Wheeler needs to be clear about his stance on diversity. Orloff said that Wheeler needs to publicly state that “it’s part of a much larger issue that we as a city are working with, and here’s what it is and how I’m going to address it.’”

Though he knows running for re-election will be hard, Wheeler seems to have chosen the high road. According to sources close to him, like Fish, he cares about the job and feels that he has more goals to accomplish.

No one knows now what will happen in the election in May, but one thing is clear: Wheeler, a politician with lofty goals, is the front-runner, and it is up to his challengers to defeat him, not the other way around.