Portland’s Mayor Is Struggling on the Job. And It’s About to Get Harder.

No man is an island, but Ted Wheeler looks marooned.

Ted Wheeler (Thomas Teal)

The swimming pool in the basement of the Multnomah Athletic Club is an unlikely setting for a breakup.

The brightly lit, 25-meter pool, kept at a balmy 88 degrees, is one of three pools in the city's best-known members-only athletic club, tucked into the foot of the Southwest Hills.

On a Sunday morning in July, Mayor Ted Wheeler was swimming laps shortly after dawn.

Wheeler, 56, enjoys a physical challenge. The mayor, who once summited Mount Everest, runs half-marathons and participates in "Iron Man" contests, and still has enough energy for a hectic work schedule.

That morning, Wheeler encountered one of the first people to help him reach Portland City Hall: John Russell, who was swimming in the next lane.

Portland Mayor Ted Wheeler swims in the Willamette River. (Thomas Teal)

In the past three decades, few private citizens have been as close to Portland mayors as Russell, 73, a real estate investor who built the PacWest Center. In 2016, Russell joined with other downtown power brokers to help end former Mayor Charlie Hales' hopes for a second term by throwing their clout behind Wheeler instead. (He gave Wheeler's campaign $1,000 that election cycle and another $5,000 earlier this year.)

Just prior to their encounter at the MAC, Wheeler had left a message for Russell, soliciting another $5,000 contribution to his re-election.

But that morning, as the two men took a break from their laps at one end of the pool, Russell had an answer for Wheeler: no.

"This city is adrift," Russell recalls saying. "It's not ambitious. It leaves the citizenry without a sense of pride about getting things done."

Wheeler responded by inviting Russell to the mayor's office to pitch ideas. At that July 16 meeting, Russell offered suggestions. Some were self-serving, like removing off-ramps from the Morrison Bridge to make his properties easier to develop. Others were civic-minded: He pitched a financing plan for paving East Portland roads, and suggested Wheeler convene a "kitchen cabinet" of unpaid advisers as a sounding board.

Wheeler just stared at him blankly, Russell recalls. And that was the last time they talked. (The mayor's office declined to answer questions about the interaction with Russell.)

Is Wheeler a better mayor than Hales, whose term was characterized by equal parts petulance and inaction? In response to the question from WW, Russell offers a simple "no."

(Justin Katigbak)

No man is an island, but Ted Wheeler looks marooned. Next month will mark his second anniversary in one of the highest-profile jobs in Oregon politics—and Wheeler is struggling in a remarkably public manner.

No one doubts his intelligence or his integrity. But nearly all of the two dozen people WW spoke to about Wheeler say those qualities are not enough. They describe a mayor unable to move the city forward on challenges large and small. He's disappointed the left and the right, while frustrating the institutional players who want to see Portland's achievements measure up to its potential.

Wheeler seems unable to take control.

Real estate developer Homer Williams says Wheeler has been overwhelmed by Portland's ills—including the homeless camps that line city streets.

"Unfortunately, Ted had to step into a situation that's rapidly turning into a crisis that's much bigger than any of us anticipated," says Williams. "It's not that he's not trying."

Wheeler is a technocrat in an era when people have picked sides. He arrived as the Trump era dawned—and divided people. No previous mayor had to deal with the anger and despair of protesters drawn downtown by right-wing extremists seeking bloodshed. And the mayor is notably unsettled by the taunts of dissenters—and he has picked public fights, including with the American Civil Liberties Union.

His former allies on the left say he abandoned them—on housing, on the environment, on cops.

"This administration ran on strong, progressive convictions," says Nathan Howard, a former Wheeler staffer who says the mayor failed to toughen inspections of housing-code violations or direct funds from new homes built after demolitions to build affordable housing. "And then the administration abandoned many of its convictions."

Portland City Council (Thomas Teal)

Right-wingers see him as a public enemy, coddling leftist protesters, keeping police from interfering with a blockade of federal immigration offices, and ignoring the proliferation of homeless camps.

"There was the hope he would be the grown-up in the room," says Jim Pasero, a conservative political consultant. "I think he strategically, when he got elected, decided to take a deep dive into the progressive end of the pool. But he is an MBA and a state treasurer, so I'm not sure it was a natural fit for him."

Wheeler's office declined to discuss the details of criticisms but says he's living up to campaign pledges.

Perhaps the biggest problem: The wonky Wheeler hasn't gotten much done.

Even in a booming economy—with two dozen cranes on the skyline—indicators show Portland adrift.

By some measures, conditions downtown continue to deteriorate. The number of used hypodermic needles picked up by Downtown Clean and Safe, for instance, will reach nearly 39,000 this year—about four times the total in 2015. The amount of garbage the group has picked up doubled over the same period. And the number of car thefts in Portland has risen by 45 percent in the past two years.

He made big promises on the campaign trail—then shelved or changed many of them. "In my mind," says Russell, "it's what he's not doing, as opposed to what he's doing."

Last week, WW asked Wheeler to grade himself on his achievements. The mayor nervously rocked back and forth in his chair with his palms together—a nervous tic that's been noticed in City Hall. He caught himself and stopped rocking, giving himself an incomplete.

"It is too early," he says, "for me to either be popping Champagne corks or berating myself for not getting something done."

The job is about to get harder.

In January, the City Council gets a new member: Jo Ann Hardesty, a longtime police critic and arguably the most left-wing commissioner on the council. She joins Commissioners Chloe Eudaly and Amanda Fritz as a voting bloc that could overrule Wheeler from his left.

On a nonpartisan council, it's as if the mayor has nonetheless managed to find himself in the minority party.

"The council as it will shortly be composed will be more difficult to lead," developer Jim Winkler says.

Jo Ann Hardesty greets supporters on Nov. 6, 2018. (Abby Gordon)

Wheeler arrived in City Hall at a time when Portland was hungry for a new course. There was also hope after the three previous mayors whiffed—Tom Potter never made a dent, Sam Adams was crippled by scandal before he began, and Hales gave up.

In some ways, Portland got what Wheeler promised. He has created a more congenial atmosphere with his colleagues than Hales did. He proved deft at assigning bureaus. He took away the Bureau of Emergency Communications from Commissioner Fritz, for instance, and the bureau has since dramatically reduced wait times for emergency calls.

"Ted has made some mistakes, but he has only been mayor for two years," says Felisa Hagins, political director of Service Employees International Union Local 49. "It's the toughest job in Oregon politics. You just have to tough it out. That's what made Vera [Katz] great."

As a candidate, Wheeler pledged to provide a shelter bed for every Portlander on the streets by the end of this year. He signed on to a "tenants' bill of rights" that included an end to no-cause evictions and a city office dedicated to landlord-tenant affairs. And he called for police reform, including demilitarizing officers and adding body cameras.

Indeed, Wheeler has struggled to meet key goals.

Last year, he abandoned his plan to provide a shelter bed for every homeless person, and now says he never meant to clear everyone off the streets. In February 2017, he passed a requirement that landlords pay moving costs in many evictions—a big achievement—but junked the idea of a robust tenant-landlord relations office. Police still don't wear body cameras, and they cracked down on leftist protesters this summer with a force unmatched in recent memory.

Russell, who has advised every mayor dating back to Katz, says Wheeler set himself up for failure.

"Wheeler announced he was going to focus on three things—affordable housing, homelessness and police relations," Russell says. "What they have in common is, they are insoluble, not that they are the wrong issues."

The mayor says he's hard at work on those promises. "I ran on a very clear platform of homelessness, housing, transportation and infrastructure, police bureau and accountability," Wheeler tells WW. "And in every one of those areas, this administration has made strong progress, but the work is incomplete."

Wheeler takes office in 2017. (Courtesy of the mayor’s office)

People trying to figure out what's gone wrong in the mayor's office see a pattern.

Wheeler starts with big ideas, but when he encounters obstacles, he stops talking to people until it's too late. Then he settles for a symbolic gesture.

"They think they can govern by sound bite," says a City Hall source. "How about they do the work—understand the issues?"

Even his allies in City Hall concede Wheeler has room to improve.

"I hope he strongly considers running for a second term," says Commissioner Nick Fish. "I'd like to see him be more proactive and less reactive in his approach to the job."

He started that pattern 11 days before taking office.

On that day two years ago, more than 60 community leaders met at the advertising firm Wieden+Kennedy, which was working on a campaign to make Portland feel proud of itself again. The ideas included broadcasting Wheeler's tweets on electronic billboards.

Wheeler arrived to make a pitch for focusing on racial equity in the first 100 days of his administration. He presented a rehearsed plan that impressed nobody.

Wieden + Kennedy’s Portland office. (Cameron Browne)

"My impression, prior to the meeting, was that he would listen," says state Rep. Diego Hernandez (D-East Portland), "but instead, he was more interested in informing the community of a predeveloped plan."

Besides one follow-up email, that's almost all any of the participants heard about Wheeler's ideas for racial equity. The inspirational campaign went into mothballs. And Hernandez got the sense Wheeler didn't want to hear about the complicated problem of race relations in Portland.

Wheeler "gave up on his commitment," says Hernandez, "after realizing that addressing historical and institutional racism wasn't as easy as providing a top-down plan."

Wheeler has admitted he handled the meeting poorly. But his top-down approach marked a pattern.

This summer, his office tried to show it was engaged on tenants' rights—a plank of Wheeler's campaign platform.

Commissioner Chloe Eudaly, TriMet, Mulrnomah County celebrate partnership that upgrades Line 73 to Frequent Service on NE 122nd Avenue. (PBOT)

For eight months, Commissioner Eudaly held meetings every other week to craft a resolution that would limit landlords' ability to screen tenants based on their criminal history.

Then in June, eight months after Eudaly launched her initiative, Wheeler submitted an ordinance duplicating her efforts. The mayor's action made him look like an ambitious student trying to claim credit for a team project. It baffled the groups doing the work.

"They had been sitting at the meetings," says one staffer at a community organization. "I'm not sure if they were trying to lay claim to it, or trying to throw shade on Eudaly's office. It came out of left field."

Wheeler's office backed off, and Eudaly's office is still pursuing the reforms.

Margot Black, an organizer for Portland Tenants United, was one of Wheeler's early supporters and helped write his platform on tenants' rights. Now she says she's disillusioned.

"He has failed to lead on anything or manifest any vision for this city besides a playground for the wealthy," says Black. "He revealed himself as the ultimate caricature of the 'liberal' Portlander whose progressiveness is only skin deep."

Margot Black (Benjamin Kerensa)

A similar dynamic occurred this spring, when Wheeler introduced a plan to require seismic upgrades for all unreinforced masonry buildings. It would have given private owners of unstable buildings a 20-year window to make them safe in case of a large earthquake.

For months, emails show, other commissioners raised questions about the cost to building owners. Wheeler didn't listen.

"[The mayor's team] seemed intent on hard-selling the policy to the council and community," wrote Marshall Runkel, chief of staff to Eudaly, in a May 1 email. Runkel wanted to know how building owners—including churches and schools—would pay for the upgrades, and if the city would help foot the bill. "The fact that the team couldn't or wouldn't answer my relatively straightforward questions is the source of my disappointment."

Two days before Wheeler's ordinance came to the council, a group of black ministers learned of the requirements that would affect their churches.

They say they summoned Wheeler for a meeting the next night at the Lloyd Center offices of the NAACP. It didn't go well.

"I would describe the mayor's attitude as 'I didn't create this mess and I'll try to navigate through it, but I don't know how to do it, other than shutting it down,'" says E.D. Mondaine, president of the NAACP of Portland. "I think, if given the chance, he'd be a wonderful second-term mayor because of all he's had to learn from his many mistakes in this term."

Wheeler settled on a compromise: a yearlong effort to look at ways to fund upgrades and passing an ordinance requiring building owners to post signs saying their structures are unsafe. But even that weak gesture is getting him into trouble. Building owners say they'll sue because the requirement is "not narrowly tailored to any substantial government interest."

The mayor's office declined to comment on any of those instances of a project Wheeler has failed to bring to fruition.

Wheeler's troubles came to a head in November, in a meltdown triggered by protesters.

Right-wing protesters on the Portland waterfront on Aug. 4, 2018. (Sam Gehrke)

For months, extremist groups regularly brawled in Portland streets at the behest of Joey Gibson, an unemployed Washington real estate broker who leads a right-wing group called Patriot Prayer. The group's clashes with masked antifascists have frightened the city, frustrated downtown business owners and seemed to baffle the mayor—who tried repeatedly to bar Gibson's group from gathering.

The mayor did nothing to create these protests, but he seems ill-equipped to address them.

Wheeler has found protesters intensely frustrating. Face-to-face interactions with the public can also get under Wheeler's skin. His least favorite part of his job? "Hecklers," he says.

His first months on the City Council were marred by escalating and disruptive protests at City Hall. In response, the council beefed up security and passed an ordinance making it easier to eject protesters from the building.

Wheeler acknowledges hecklers' tactics alarm him.

At a recent community meeting for a homeless shelter, he showed up with Multnomah County Chairwoman Deborah Kafoury to a room of a couple hundred people.

"I was literally counting the steps, wondering whether the chair and I could actually make it to the exit," Wheeler tells WW. (Kafoury declined to comment.)

Multnomah County Chairwoman Deborah Kafoury (Multnomah County)

Wheeler's fears may play into his unwillingness to push for the police reforms he promised as a candidate. Riot cops have deployed "flash-bang" grenades and other crowd-control devices on leftist protesters when the cops felt events got out of hand.

"What we've seen in the first two years is the police continue to be heavily militarized and heavy-handed in their approach to protests," says David Rogers, executive director of the ACLU of Oregon. "Which is expensive, dangerous and threatens our democracy."

In October, Wheeler decided he needed to separate the warring street protesters.

"I approached that with a sense of passion and urgency, as did the [police] chief," Wheeler tells WW, "and we were very, very concerned about what we were hearing about the Proud Boys coming back to Portland."

Wheeler pushed forward without first building support among his colleagues and interested community groups. His top-down approach didn't work.

"We've tried really hard to work with him," says Zakir Khan, board chairman of the Muslim civil rights nonprofit Council on American-Islamic Relations Oregon. "Why do all that if we are going to feel like we're just being strung along? Why go into public service if you're not trying to serve the public?"

Rogers says he hopes the mayor engages in some self-reflection. "We hope that moving forward," Rogers says, "he moves away from a cavalier approach and the politics of division."

The result: The City Council voted down his proposal 3-2.

Left-wing protesters on Aug. 4, 2018. (Justin Katigbak)

Eudaly says Wheeler must listen more.

"As much as I want to support the mayor and see him succeed, I need to know that every piece of legislation we advance is the best we can do and that we're prioritizing the most urgent issues," she says. "That's hard to achieve without meaningful engagement on issues and policy solutions."

The mayor concedes he bungled the protest rules.

"I didn't bring my colleagues along," he says. "My entire team will be working doubly hard to make sure we never surprise our colleagues, particularly on big stuff, even if there is a sense of urgency."

A day later, Wheeler faced more heckling.

At the Oregon Health Forum on Nov. 15, Wheeler faced a confrontation with someone yelling at him from the crowd who objected to how police clean up homeless camps.

Wheeler responded saucily.

"What is the law?" the mayor asked.

"I don't know,"  the heckler answered.

"I do and I am about to tell everyone in this room," Wheeler shot back.

At another interruption, he asked the heckler, "Do you want to give the speech?"

The fight apparently left him out of sorts. After a question-and-answer session in which he was challenged to do more about cleaning up tents, Wheeler was overheard mumbling that he couldn't wait for his term in office to end.

(Thomas Teal)

Wheeler, who didn't endorse in the commissioner race between Jo Ann Hardesty and Loretta Smith, may now find himself a mayor riding in the back seat of his own City Council. Hardesty won endorsements from the other two women on the council, and on some issues at least, the three are likely to vote as a bloc.

On election night, Hardesty expressed her eagerness to work with her fellow commissioners and "Mayor What's His Name." (She later apologized for the gaffe.)

"On day one," she said, "we get to show what real governance looks like. We get to show what happens when you listen to the people who you're governing."

Eudaly rejects the idea that the majority-women council will be in consensus. "Anyone who's been paying attention will know Commissioner Fritz and I don't always agree," says Eudaly. "That is not going to magically change with the introduction of a third woman. I believe the three of us share some common values and priorities around community engagement, equity, police reform, people over profit, and breaking down barriers to participation in our electoral system."

Hardesty pledged to withdraw Portland from the Joint Terrorism Task Force, a multiagency law enforcement partnership run by the FBI. Wheeler supports Portland's participation in the JTTF. But the mayor has signaled that Hardesty has the votes to end the partnership—and has already met with the FBI about the logistics of withdrawing.

Jo Ann Hardesty (Abby Gordon)

The contract with the police union is up for renegotiation. It seems unlikely Wheeler will be able to find support for salary increases, unless he can point to substantive reforms at the Police Bureau.

The mayor downplays the challenges of Hardesty's arrival.

"On some issues around public safety, we will probably have disagreements, but that's just part of the way it works here," says Wheeler. "It's crazy to assume we are going to agree on everything all the time. So I will probably, in some cases, find myself in a minority position and other cases not."

Wheeler is not giving up on the idea of his campaign promises coming to fruition—and continuing to lead Portland. In fact, he claims he'll run for another term.

His message to Portland: You're going to have Ted Wheeler to kick around some more.

"I'm not going to make an announcement today, because my wife and my daughter have a right to be engaged in the decision when I make it, and I'll make it during 2019," Wheeler tells WW. "But people should absolutely expect I will not only run for re-election, but I will run an aggressive campaign, and I will put a very aggressive, forward-looking agenda on the table."

The nonprofit WW Fund for Investigative Journalism provided support for this story.

Wheeler once seemed poised to become Oregon governor. But Kate Brown got the gig. (Justin Katigbak)

Ted Wheeler's History Led Him to Expect Better Things

The job of Portland mayor was a fallback for Ted Wheeler—like a safety college for a straight-A student. And that might explain his disillusionment with how tough a job it is.

Twelve years ago, Wheeler breezed into office at the age of 43 to a relatively high-level position for a first-time elected official: Multnomah County chair.

He's a sixth-generation Oregonian, the son of a wealthy timber family for whom the town of Wheeler, Ore., is named. After graduating from Stanford, he earned an MBA from Columbia University and a master's in public policy from Harvard. He wrote a book about good government, but worked for two decades in the private sector. He's not a career politician who came of age on compromises and negotiations; instead, as a millionaire, he's never had to worry about holding down a job.

"Few mayors have been as well-prepared as Ted Wheeler at knowing how to run municipal governments," says the real estate magnate and philanthropist Jordan Schnitzer.

In 2010, then-Gov. Ted Kulongoski appointed him state treasurer, after the death of Treasurer Ben Westlund. Some observers believed that made Wheeler heir apparent to Gov. John Kitzhaber, who was then running for election to a nonconsecutive third term.

When Kitzhaber abruptly resigned in 2015, then-Secretary of State Kate Brown became governor instead, dashing Wheeler's hopes.

He set his sights on the next best available position: Portland mayor.

In his first two elected jobs, Wheeler earned high marks for his brains and technical expertise, but low marks for collaboration. That was a red flag: Portland is a city of civicly engaged people who want a say in how their city is run. And in Portland's weak mayor system, he would be just one of five votes on the City Council, not the undisputed boss as he was at Multnomah County and the state treasury.

As treasurer, Wheeler would at times develop an ambitious idea, then drop it.

He proposed a 2014 ballot measure to make college more affordable. Called the Oregon Opportunity Initiative, it would have required the state to borrow money to create college scholarships. Wheeler failed to raise adequate campaign contributions and it failed badly at the ballot box.

"I don't consider it a failure in that it opened up a conversation," Wheeler told WW in 2016. "It was a big idea, and sometimes it takes more than one shot to get a big idea through."

Some had their doubts, including Portland State University administrator Sarah Iannarone, who ran against Wheeler in 2016.

"I wanted to force a dialogue about whether Ted Wheeler possessed the vision, the temperament, and the essential knowledge to govern us effectively at a critical juncture in our history," Iannarone says. "I predicted he didn't, and, well, the rest is history."

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