Portland just elected its fourth new mayor in four election cycles. Will Ted Wheeler stick around?

Not since 2000 has Portland re-elected a mayor.

That year, voters sent George W. Bush to the White House and then-Mayor Vera Katz back to Portland City Hall for a third term.

Portland has weathered a succession of one-term wonders ever since. Now, as Mayor-elect Ted Wheeler prepares to enter office in January 2017, having won the May 2016 primary election outright, the question on everyone's mind is: Will he succeed in winning a second term? Will he even seek one?

"I don't make predictions about the future," Wheeler says, "but ideally this would be an opportunity where I'd be engaged over the long term."

Wheeler, Oregon's state treasurer and a former Multnomah County chairman, faces numerous challenges when it comes to keeping the support of Portland's progressive electorate.

Tom Potter followed Katz as Portland mayor in 2004. Having served as Portland's police chief from 1990 to 1993, Potter was well acquainted with Portland's unique—some say nutty—commission form of government, which gives four city commissioners who are elected citywide nearly as much power as the mayor. Yet he found the system unwieldy, a fact that he illustrated vividly by storming out of a November 2007 City Council session after declaring himself "irrelevant" to the discussion at hand. Potter opted not to run in 2008.

That cleared the way for then-Commissioner Sam Adams, who bulldozed Potter's candidate, Sho Dozono, in the May primary, winning 59 percent of the vote to become the first gay mayor of a large American city. But Adams, as nearly everyone by now knows, squandered the promise he had by lying about the sexual nature of a relationship he had with a teenage legislative intern a few years earlier, when Adams was 41.

WW broke the news that Adams had lied about that relationship with Beau Breedlove in 2009, just days into Adams' term as mayor. It didn't matter that a state investigation later found "insufficient evidence" to charge Adams with a crime. In 2012, Adams declared he couldn't run the city while fighting for re-election, so he bowed out of the campaign.

In walked Charlie Hales, also a former city commissioner. Pitching himself as a grown-up version of Adams—who had pushed innovative environmental policies such as curbside composting and a ban on disposable plastic grocery bags, but failed to prioritize spending on basic city services—Hales appeared to have staying power. He handily beat then-state Rep. Jefferson Smith (D-Portland) and businesswoman Eileen Brady in 2012. But Hales angered colleagues and alienated key constituents with his go-it-alone style of politics, proposing new taxes and other bold policy shifts without seeking city commissioners' advice. As his first term came to an end, Hales faced a problem similar to Adams'. Polling showed his chances of re-election were low.

What unites Potter, Adams and Hales?

"Each of those three," Wheeler says, "left for very different reasons."

Yet all of them confronted one central challenge: The job of Portland mayor requires working well with the four city commissioners who wield considerable power over the mayor's budget and agenda.

So will Wheeler stick around?

He says he at least recognizes the natural hazards at Portland City Hall, where issues of housing and homelessness dominate.

"The challenges facing the city of Portland are significant," he says. "The next mayor will have to do a much better job than previous mayors of managing the dynamics of the City Council, and that means coalition building, that means communication, that means not surprising colleagues with grandiose ideas without their input."

Wheeler, whose ambitions to one day be Oregon governor are well known, isn't making any promises about whether he wants to run for mayor in 2020. In fact, he seems to be hinting he may not. "I know people who have won elections who have been lousy public leaders," he says, "and I know people who have lost elections but have gone on to do brilliant things to support the community."

He adds: "I don't think it's so much quantity as it is quality."