In 1985, a young Ted Wheeler consulted experts. He read reports. Then he opened a video rental store.
While an undergraduate at Stanford University, Wheeler bought Palo Alto Home Video, a mom-and-pop shop near campus whose customers included Steve Jobs.
"I had a great vision," says Wheeler, now Oregon's state treasurer. "I wanted to have the largest video-rental collection in the entire Bay Area." (He won't say how much he paid.)
And he wanted to do it on his own.
Wheeler carried the benefits and burden of a family legacy—generations of Oregon lumbermen who built mills, cut down Douglas fir trees and helped turn them into grocery bags, corrugated boxes and particleboard. The Wheelers' company merged with others to become in 2000 one of only two Fortune 500 companies in the state. (The other was Nike.)
But Wheeler, now 53, set out to prove himself apart from his family. "Not a dime came from Mom and Dad," he says.
Wheeler's grand plan had a problem. His store rented Betamax cassettes. But people wanted VHS. So Wheeler pivoted, and shifted his company to one that hired out employees to video-tape customers' weddings and bar
mitzvahs. He later sold the business.
Wheeler says he learned "you can't get too married to your original plan. You have to be open-minded to other opportunities as they come your way."
It's an apt maxim for Wheeler's personal and political trajectory.
For 10 years after graduating from Stanford, Wheeler hopscotched from one pursuit to another. He went to Columbia Business School, then Harvard's Kennedy School of Government. He led a civic association, launched a newspaper, lectured at a Boston university, wrote a book, ran unsuccessfully for the Boston City Council, bought and renovated a shopping mall, and worked in finance. (See sidebar.)
"I was exploring different paths," Wheeler says, "pursuing different interests and passions, any one of which might have led to something. A lot of them led to nothing."
He returned to Oregon in 1997 to work for his older brother's money management firm, then opened his own investing business. In 2006, at age 43, he launched a political career, winning a bid for the Multnomah County chairmanship.
Wheeler's latest improvisation has him gunning to be Portland's mayor.
By many measures, Wheeler seems a good fit for the mayor's office (which will have its primary election May 17). Wheeler was once registered as a Republican, but his politics now check most of Portland's progressive boxes.
A close examination of his record shows that he is one of the state's more accomplished technocrats. He is smart and polite and comes to every forum armed with audits and data. This is, after all, a man who authored a book about good government before he had ever served in one.
At the same time, Portland's "weak mayor" system demands the ability to bring people along. Every proposal by the mayor requires three of five votes from colleagues to pass.
"There's a huge premium on collaboration," says City Commissioner Nick Fish.
That could be a problem for Wheeler.
As county chairman and state treasurer, Wheeler has struggled to score victories when winning required more than posing the best argument. When it comes to building coalitions to make things happen—whether reforming the county's jails or the state's investment practices—Wheeler has achieved few successes.
WW spoke with more than two dozen current and former colleagues of Wheeler's. A common theme emerged among critics: Wheeler has a habit of getting so focused on his own goals that he can forget to include allies in his plans.
"He gets on a roll," says Joe Baessler, political director for Oregon's council of the American Federation of State, County and Municipal Employees, "and he skips a step." (AFSCME endorsed both Wheeler and opponent Jules Bailey.)
Others, who asked for anonymity because they don't want to alienate one of Portland's mayoral front-runners, are harsher.
"He wants to be the smart guy in the room," says one Salem insider. "He hasn't been tested in the art of how to make a deal."
Wheeler has forged an unusual political path by trusting his own ideas above all else. Now he must convince Portlanders that he can listen to other people and find common ground.
But he's not apologizing for his track record.
"There are probably episodes one could point to and say, 'Yeah, I came in with my idea and I pushed it hard,'" he says. "If you want to be a good leader you also have to advocate for what you believe in."
Wheeler would like voters to see him as someone who will listen to their frustrations and desires.
On a recent windy afternoon during rush hour, Wheeler stood at the corner of Southeast Stark Street and 79th Avenue in the Montavilla neighborhood, talking to an African-American man who declared he'd vote for Donald Trump as payback for slavery.
Dressed in a blue button-down shirt under a gray overcoat, Wheeler listened politely, even as the man went on to discuss his dislike for Hillary Clinton, whom the man called "Hitlery."
Wheeler rarely interjected, but occasionally steered the conversation to safer ground. "Haven't we met before?" he asked.
About two hours earlier, Wheeler's campaign had plopped down a wooden desk outside the Bipartisan Cafe on Stark Street and announced on Twitter that Wheeler's "office hours" were open. In small groups or individually, people showed up. Their concerns mirrored those echoing throughout the campaign: air pollution, housing affordability, density.
Michael Brassell, who said he was torn between voting for Wheeler and Bailey, told Wheeler he didn't think Portland was doing enough to curb rent hikes. "So what kind of ideas are you talking about?" Wheeler wanted to know.
RoseMarie Opp, a Mill Park resident, urged Wheeler to do more to protect Portland's Bull Run water supply—and fight to keep open reservoirs. "They should not just be destroyed," she said.
"If you think there are strategies we could still use," Wheeler told her, "I'd love to learn about that."
Four years ago, Mayor Charlie Hales pitched himself as a Mr. Fix It, who would fill potholes, balance the budget and improve policing. Today, Wheeler's platform focuses on the social ills that have captured voters' attention.
These are themes Wheeler outlined in his 1993 book, Government That Works: Innovation in State and Local Government, which looked at creative public policy solutions to problems such as drug abuse, inequality and inadequate housing.
The book isn't so much a "how to" as a series of case studies—San Diego's effort to preserve single-room-occupancy hotels, Vermont's scheme to give low-income housing tax credits to private companies that invest in affordable housing, and Massachusetts' efforts to enforce fair housing laws with penalties that provided funding for more enforcement.
But one idea runs throughout the book. Wheeler sums it up on the third page: Smart ideas can trump politics.
"The public sector," he says, "can be innovative, well-managed and effective, even when it comes to solving particularly vexing problems."
"He brought things together"
Wheeler walked into a Multnomah County chair's office in 2006 that looked about as inviting as a grizzly's lair. Three of the female commissioners had been dubbed "mean girls" for their disagreements with former Chairwoman Diane Linn. County Sheriff Bernie Giusto was in the news for alleged abuse of power.
Despite these challenges, Wheeler mostly flourished at the county, guiding the agency through a recession that squeezed budgets in all departments.
"He brought things together," says Lisa Naito, a county commissioner who served with Wheeler for two years. "He's analytical in a good way. He does his homework, and he always did a very good process. I think he's really a great public servant."
In office, Wheeler delivered east county its promised courthouse, brought transgender health benefits to county employees and ended the practice of asking job applicants about their criminal history. (Years later, Portland City Hall would copy the latter two efforts.)
The county chair enjoys tremendous authority over budgets and hiring—more than Portland's mayor. The courthouse project easily won county commissioners' support, and Wheeler enacted the other two by executive order.
But on other issues that required winning support from outside groups, Wheeler was less triumphant.
In 2007, partly in response to Giusto's troubles, Wheeler pushed to take power from the county sheriff, whose budget of $90 million composed about a quarter of the county's overall budget but received little oversight from Wheeler and his fellow commissioners. (Giusto famously dismissed the commissioners as his "bankers.") Wheeler wanted to make the elected county sheriff an appointed position, a move that would have required changing state law.
Wheeler left county office in 2010 without securing a change. The Oregon State Sheriffs' Association panned his idea, and the citizen commission of volunteers tasked with reviewing the proposal balked.
"I ran up against everybody," Wheeler says. "I was completely alone."
Another project, the building of a new Sellwood Bridge, has a more complicated legacy.
Last week, County Chairwoman Deborah Kafoury, who worked with Wheeler as a county commissioner from 2008 to 2010, endorsed County Commissioner Jules Bailey for mayor. Her move was surprising to some. But to others, the decision has roots in the new Sellwood Bridge, which opened last month.
In Wheeler's campaign literature, he lists the financing of the new Sellwood Bridge as one of his accomplishments as county chairman, saying he "funded a backlog of infrastructure needs, including the Sauvie Island Bridge, Sellwood Bridge and East County Courthouse."
A number of observers dispute that.
The bridge project required joint funding from Portland City Hall. Former City Commissioner Randy Leonard says he found Wheeler to be thoughtful and dedicated, but says Wheeler's efforts to secure city funding for the bridge were often "counterproductive."
Amid negotiations in 2009, Wheeler came to a public meeting at City Hall and scolded then-Mayor Sam Adams and Leonard for their support for using $15 million in urban renewal funds to renovate a stadium then called PGE Park so the Portland Timbers could join Major League Soccer.
Wheeler, in other words, alienated two people just when he needed them. "He was blowing up a deal that had enormous implications," Leonard says. "It felt to me at the time it was a 'gotcha.' I think about it even now and I shake my head about how he was so shortsighted."
It wasn't until 2011 that the county finally inked a deal on the Sellwood Bridge financing, after Kafoury repaired relationships.
Leonard adds: "That bridge would not have been rebuilt if Deborah Kafoury was not on the county commission."
Wheeler brushes off questions about his leadership, saying he doesn't care who gets credit for the Sellwood Bridge.
"My name is not on the bridge, and I don't give a damn," he says. "All I care about is that when I go across it or my daughter rides her bike across it, she's not going to get killed. That's how you get stuff done in the public sector. People are not going to remember my name, and I'm totally OK with it."
Time at the treasury
Wheeler's six years as state treasurer are largely perceived to have been competent.
He took office in 2010, when then-Gov. Ted Kulongoski asked Wheeler to take the job after the death from cancer of Treasurer Ben Westlund.
Wheeler's brand of nerdy earnestness worked in the treasurer's office, where the central function is to safeguard Oregon's investment portfolio of $90 billion, including Public Employees Retirement System funds.
In this obscure but critically important function, "he's done an excellent job," says Bill Parish, a local investment adviser who closely watches the treasury's investment council.
In the past 10 years, Oregon's returns have put it at the top among peers.
But the treasurer does more than act as banker, and when Wheeler needed to deal with the Legislature, he suffered.
After he blasted the Legislature in the media for its sluggishness, Wheeler's relationship with Senate President Peter Courtney (D-Salem) was rocky at best.
Courtney declined to be interviewed. But it's clear this poor relationship was damaging—among other things, it stalled Wheeler's efforts to reform the treasury office, which he says would have saved money and increased efficiency. But the proposal would also have given the office more independence.
"This wasn't just some trip down the rabbit hole," he says. "This was backed by multiple external reviews, as well as our own internal audits."
Still, it was complicated, and many observers didn't see the value in reducing legislative oversight. Jim Hill, a Democrat who was Oregon's treasurer from 1993 to 2001, says he didn't get it. "I was very puzzled by it," he says. "When you introduce a bill that calls for less oversight on a multibillion-dollar fund, that is very strange."
Wheeler failed to get it through the Legislature not once, but three times.
"Ted suffers from the deficit of never having served in the Legislature," says former Rep. Vicki Berger (R-Salem). "The handling of that, to me, showed that that hurts."
Wheeler's most public failure at the treasury was an unsuccessful effort in 2014 to pass a ballot measure in support of college affordability. The Oregon Opportunity Initiative would have borrowed money to create a dedicated fund for college scholarships. He won few editorial endorsements (WW supported it) and ran a breathtakingly lackluster campaign, raising just $80,000.
Voters rejected the ballot measure with 57 percent of the vote.
"I don't consider it a failure in that it opened up a conversation in Oregon about the lack of support for student financial aid and the increasing indebtedness that our students were facing," he says. "It was a big idea, and sometimes it takes more than one shot to get a big idea through."
"It's about building consensus"
Wheeler says a decade of public service has taught him to seek out diverse opinions. He says he understands he'll need to use persuasion as Portland mayor.
"It's a leadership position," he says. "It's not where you come and say, 'Make it so.' It's about building consensus for three votes, and that means you have to be collaborative, you have to communicate, and there can't be surprises."
But moments on the campaign trail suggest the earnest policy wonk—whose bumper stickers declare he'll be Portland's "nerdy mayor"—still hasn't fully absorbed the lessons of the past 10 years.
On March 18, Wheeler walked into the office of the Portland Development Commission to meet with 40 or so PDC employees during their lunch break.
The employees, members of the American Federation of State, County and Municipal Employees Local 3769, had invited Wheeler to talk about his vision as mayor—a critical question as the PDC faces its own uncertain future. Last month, its executive director, Patrick Quinton, announced he would leave in May. Meanwhile, the agency faces budget cuts as urban renewal funding dries up.
Over brownbag lunches, Wheeler offered little comfort, according to two people who were present at the meeting. Instead, he criticized PDC for failing to secure a Trader Joe's outlet on city-owned property in Northeast Portland in 2014, then bungled a question about PDC's budget, giving some in the audience the impression he would pull funding if he didn't get to appoint the next executive director.
"It didn't go well," Wheeler acknowledges, adding he never meant to give the impression funding was tied to the appointment process.
"My intention was to inspire them," Wheeler says. "My comments struck some as being dismissive of the good work they're already doing."
But Wheeler has at least learned the Portland way of saying sorry. The following Monday, Wheeler went back, this time with Voodoo doughnuts and an apology.
He plans to return a third time, promising to talk less and listen more. "What I've asked them to do," he says, "is give me their best shot at what they'd like to see improved and how I could be helpful as the next mayor."