Ted Wheeler's biggest challenge in mayoral race -- his own to-do list

Ted Wheeler had been canvassing in Southeast Portland without much luck before reaching a century-old farmhouse swallowed up by decades of modern development.

The long-time owner, a rare voter home on a sunny weekday afternoon, was full of questions: What are you going to do about home demolitions? How will you create jobs? What's your stance on taxes?

Wheeler's answers didn't matter all that much. Soon after, 74-year-old John Anderson complimented Wheeler for his stint as Oregon treasurer, which followed an even more notable tenure leading Multnomah County.

"I assume you're going to get elected," Anderson told the mayoral frontrunner.

"I do, too," Wheeler answered.

And so it is with Wheeler, one of Oregon's most ambitious and highest-reaching politicians -- but also someone whose political arc has been relatively unchallenged.

Wheeler, 53, has amassed one of the most impressive resumes of anyone running for Portland mayor in a generation. Advocates praise his level-headed leadership and detail-oriented management. None of Wheeler's 14 opponents come close to possessing his financial or executive background - a point Wheeler hammers on the campaign trail.

But Wheeler owes his political success to good timing and flawed opponents as much he does to his own muscle and risk-taking. He won Multnomah County office 10 years ago by trouncing a weak incumbent. He rose to treasurer thanks to a gubernatorial appointment. And Wheeler launched his mayoral campaign against someone whose brief stint atop Portland government produced a growing list of enemies, leading Mayor Charlie Hales to ultimately drop his re-election bid.

Wheeler's blind spot, according to interviews with more than 15 people who know or work with him, is that he often gets caught up chasing his own ideas, lacking the desire -- or disregarding the need -- to work collaboratively to win people over. In Portland's peculiar form of government, where the mayor is not the chief executive, teamwork is essential to political success.

Over the years, Wheeler hasn't delivered on some of the biggest endeavors of his career when obstacles emerged -- failing to open the still-unused Wapato Jail, restructure the Multnomah County Sheriff's Office, secure legislative support to revamp the Treasury or win voters' approval to help pay college tuition through a state endowment.

"I didn't get into politics so that I could take little bites around the edges," Wheeler said in a recent interview from his eastside office overlooking downtown. "My goal is to always be a transformational leader, and to go big. And when you go big, you don't always win. And I'm OK with that."

This year, Wheeler's making big campaign promises, too, none greater than having shelter by 2019 for an estimated 1,900 Portlanders sleeping outside. On doorsteps, debates and in driveways - just like where he pitched Anderson, off Southeast Belmont Street - Wheeler outlines all the ways he wants to improve Portland. But can he deliver?

"Are you going to forget about all us commoners," Anderson asks, somewhat jokingly, "when you get elected mayor?"

The family business

The Wheeler family legacy begins 60 miles west of Portland, in a town where tree-lined hillsides and the Nehalem River meet the Pacific Ocean. It was here, a century ago, that lumber mills helped feed Portland's growth under the watch of the town's namesake: Coleman Wheeler, Ted Wheeler's great grandfather.

Wheeler's grandfather and father tracked into logging, merging with other businesses to create Willamette Industries in 1967. It grew into one of Oregon's few Fortune 500 companies, scooped up by Weyerhaeuser in 2002 as part of a $7.9 billion deal.

Wheeler never showed much interest in the family business.

Wheeler's parents divorced in 1972, when he was 10. Wheeler said that, for a time, he resented and was angry with his father. Sam Wheeler, he said, was an alcoholic who didn't address his addiction until his son was in college.

As a boy, Wheeler was easygoing and didn't cause trouble, mother Leslie Wheeler recalls. In part, she chalked it up to birth order, buying each of her four boys signs for their desks at home.

"I'm No. 3, and I don't even try," read Ted's.

But the sign belied an adventurous, competitive streak. While bum ankles kept Wheeler from running cross country for Lincoln High School, he became an accomplished distance freestyle swimmer and trekked with his father on grueling hikes. Meanwhile, Wheeler became senior class president.

Then it was off to Stanford University, where Wheeler earned a degree in economics. He later moved east to attend Columbia University, then Harvard University, earning master's degrees from both.

While in Boston, he taught at Northeastern University, down the hall from former Democratic presidential candidate Michael Dukakis. He published a book in 1993 examining innovation in government. At age 30, he ran for the Boston City Council but finished second-to-last in a crowded field.

Wheeler said he loved teaching. But one day, Leslie Wheeler remembers getting a phone call from her son, whose business side kicked in. He'd been adding up all his time preparing for class, grading papers and sitting through office hours.

"You know, I think I'm really worth more than $1 an hour," she remembers her son announcing.

In 1994, Wheeler formed a company that bought and rehabbed a strip mall in Maine. Three years later, he returned to Portland and joined his oldest brother's investment firm, Copper Mountain Trust, where he remembers having a simple directive: Keep big institutional investors happy.

Wheeler said his father's family paid for his education but didn't help him financially with business endeavors. Wheeler said he inherited an undisclosed sum from his grandfather held in various accounts, but only after his father's death in 2011.

"I did not inherit a single dime from my father," Wheeler said.

But Wheeler later acknowledged - only when directly asked - that he owned an undisclosed number of shares from the family business, Willamette Industries, gifted to him over the years. Wheeler said those shares were converted to cash when Willamette Industries was bought out, although he declined to say how much he received or when.

Asked how old Wheeler was when he became a millionaire, he responded: "I don't think what's in my pocketbook matters."

Wheeler soon found fresh challenges.

In 2002, in a well-told story, Wheeler summited Mt. Everest. What's not as well-known: He suffered frostbite on his face when he was caught in a sudden blizzard, and a climber camping on the same part of the mountain - the Lhotse face - died the next day in a fall minutes ahead of Wheeler.

"We had an epic 48 hours," said Kevin Flynn, Wheeler's climbing partner, who praised Wheeler's calm demeanor under duress. "People were pretty concerned about us."

Later that year, Wheeler formed his own consulting and investment company, calling it Lhotse Capital Management. The label had nothing to do with conquering the world's tallest peak, he said.

"It's a beautiful mountain," he said, "and I like the name."

Working with grace

Wheeler opened his political career in convincing fashion 10 years ago this month, besting incumbent Multnomah County Chairwoman Diane Linn by a whopping 46 percentage points.

Race for mayor

Name:

Ted Wheeler

Age:

53

Family:

Wife, Katrina, homemaker; 9-year-old daughter

Education:

Bachelor's degree, Stanford University; master's degree in business administration, Columbia University; master's of public policy, Harvard University

Work history:

State Treasurer, 2010-16; Multnomah County chairman, 2007-10; business owner and investor, 1994-2005

Quote:

"If there's one hallmark of my form of leadership, I try to be ahead of the curve, not reactive to the problem that's already facing us."

Marred by infighting, the county board under Linn was dubbed the "Mean Girls." Wheeler, who'd never before held elected office, brought a calming presence as the county's chief executive.

"It was tough times, and he handled himself gracefully," said county Commissioner Judy Shiprack, who worked with Wheeler after she won election in 2008. "He helped the entire Multnomah County board change not only the way we're perceived in the community, but the substance of our ability to work together."

Wheeler is a self-proclaimed nerd who dives into details, yet he's also quick to put people at ease with a self-deprecating humor. He needed a little of both dealing with Multnomah County's budget, where he faced a $15 million shortfall in his first year and later had to negotiate with unions to sacrifice pay raises amid the recession.

"And nobody wanted to kill him!" said Alan Ferschweiler, president of the Portland firefighters' union, which offered a dual endorsement this year of Wheeler and his most prominent mayoral opponent, Multnomah County Commissioner Jules Bailey. "I just can't get away from that."

Wheeler also pushed progressive policies. In 2007, he removed questions about criminal history from employment applications and ensured that Multnomah County would provide full healthcare for transgender employees.

"I didn't talk a lot about it," Wheeler said of his so-called ban-the-box effort. "I just did it."

That record of accomplishment was enough for Gov. Ted Kulongoski to appoint Wheeler state treasurer in 2010, after the death of Ben Westlund. There, some considered him to be less political and more authentic than the ordinary politician, a refreshing change in Salem's halls of power.

Among his accomplishments, Wheeler launched a state-run retirement program for private-sector workers whose employers didn't offer one. He pushed for an investment fund to fuel start-up businesses. The state's $89 billion investment portfolio was named financial plan of the year for 2016.

At times, he showed a knack with lawmakers, too.

Sen. Sara Gelser, D-Corvallis, wanted to allow families to save money for disabled children without worrying that those savings would disqualify them from certain health-care benefits. But the federal government had to act first.

Within an hour of President Obama signing off, Wheeler was on the phone with Gelser, even though they'd never talked about it before.

"It told me that he knew me, and he paid attention to the values that were important to me," she said. "It also showed me he was willing to do the right thing, even if there was no political benefit to him."

Underestimating challenges

On other fronts, however, success has been elusive.

While running for county chairman, Wheeler pledged to open the mothballed Wapato Jail. Although he set some money aside, a full plan never emerged, and the jail remains closed.

Similarly, Wheeler pushed a proposal to transfer jail oversight to the county board, and to transform the post of sheriff from elected to appointed. But that didn't happen, either. The status of the sheriff remains a controversial topic, with the job's current holder embroiled in scandal.

Wheeler also pitched a regional transportation authority to pay for a new Sellwood Bridge. It went nowhere. He nonetheless brings up the same idea when suggesting ways to help pay for Portland's crumbling roads.

"When something doesn't work, it doesn't mean I walk away from it," Wheeler said. "It just means it didn't work, and now we try something else."

Wheeler tried three times, for instance, to revamp the Treasury, hoping to secure autonomy from the Legislature to cut down on Wall Street management fees. In 2014, Wheeler's office said the changes could save $2.8 billion over 20 years.

Among the critics: Sen. Chris Edwards, D-Eugene, who said he figured that Wheeler would make efforts to assuage his concerns. Edwards said he worried the move would diminish public accountability by putting investment staff under an investment council, rather than the treasurer. But conversations never happened.

"He definitely thought it was the right policy call, and how could you argue with the right policy call?" Edwards said. "He underestimated the level of concern that some of us had with the bill, and assumed that we would fall in line. And that just wasn't the case."

Wheeler said he and his staff put in countless hours winning over opponents, including one key power broker, Sen. Richard Devlin, D-Tualatin, a leader of the Legislature's budget-writing committee.

"At the end of the day, one legislator killed it: Peter Courtney," Wheeler said of the Democratic Senate president. Courtney did not respond to an interview request.

Wheeler dismissed any notion that he didn't collaborate to win support. "I bent over backwards so far that I hit my forehead on the ground," he said.

Another high-profile dud was Wheeler's state ballot measure two years ago.

He wanted to borrow money to create a $100 million endowment, using investment proceeds, to cover grants for college students. Wheeler formed a campaign committee and raised nearly $57,000 in six months.

But then, in the seven months before the election, he collected less than $22,000. In November 2014, voters panned it.

"He was sincere in thinking this was a good deal," said Steve Buckstein of the Cascade Policy Institute, the only group that opposed the measure. "But I think he realized early on that it was not going to pass."

Wheeler blamed a confusing ballot title, not a lack of effort, for killing it.

"It was just too complex and the ballot language stunk," he said. "I absolutely did not give up."

Bigger plans

Heading into the May 17 election, Wheeler finds himself with a sizeable lead, according to limited public polling data. He's also established a massive fundraising advantage with $812,000 in cash contributions, nearly six times what Bailey's pulled in.

"Ted's been skillful at walking that tightrope of being able to keep his more moderate, business-friendly constituency on his side but also being able to find opportunities to appeal to people who are more progressive in the community," said John Horvick, political director for polling firm DHM Research.

If Wheeler wins, he's already set a long to-do list.

Among other things, his pledges include:

Making east Portland the top funding priority in the parks budget; increasing east Portland's tree canopy by 10 percent in three years; offering a plan for citywide bus rapid transit service; proposing incentives for businesses to replace old diesel engines with newer, clean models; hiring the "most racially and socioeconomically diverse administration in city history"; ensuring enough shelter space for homeless Portlanders by the beginning of 2019; and paying for skills-training that helps 25,000 Portlanders find jobs offering $25 an hour by 2025.

Wheeler said he's confident he can deliver and hasn't made too many promises.

Yet some wonder how long Wheeler would stick around. Portland's past three mayors, including Hales, will have all left City Hall after just one term. Wheeler has openly coveted the governorship -- finding his path blocked by fellow Democrats John Kitzhaber and now Gov. Kate Brown. The office could be open again in 2022.

Asked if he still wants to be governor, Wheeler said, "less so than I did before." But, assuming he wins his Portland race, Wheeler was unequivocal during a late April interview about being mayor: "I'm not committing to a second term here today."

The people of Portland could use some stability, city Commissioner Steve Novick said.

"Being mayor will make it really hard to be governor," Novick mused last fall, on the day that Hales dropped out of the race. "Because if you're a Democrat running statewide, you've got to get 75 percent of the vote in Portland. And if you're mayor, you've probably ticked off more than 25 percent of the people.

"It wouldn't surprise me, if he won, if Ted concluded: 'Actually, I better stick in this job.'"

--Brad Schmidt

503-294-7628

@cityhallwatch

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