BY GORDON R. FRIEDMAN

Few decisions by Portland Mayor Ted Wheeler divided the city as much as his plan to impose controversial restrictions on the high-profile protests that have bloodied participants – and his reputation.

Wheeler staked much of his political capital on the idea, appearing on NBC to explain to a national audience why his plan was both constitutional and smart.

Still, the mayor knew getting his proposal passed would not be easy. He surprised his City Council colleagues when he presented it to them only hours before unveiling it publicly. He was aware some city commissioners vehemently opposed it.

And in perhaps the greatest misstep of the mayor’s first two years in office, Wheeler failed to ensure he was on the same page with his hand-picked police chief, Danielle Outlaw. The first sign of disagreement happened hours before a crucial Nov. 8 public hearing.

Wheeler and Outlaw separately gave interviews to reporters beforehand. Wheeler said the protest limits plan was Outlaw’s idea, but she promptly responded that that was not the case, saying it “came from the mayor’s office.”

If there was any question whether Wheeler and Outlaw were working from the same script, it would be answered privately that evening.

Commissioner Chloe Eudaly eviscerated Wheeler’s proposal during the long public hearing. Reading from a list of prepared questions, Eudaly grilled Outlaw and other top police brass about officers’ use of force against protesters, perceptions of police bias favoring right-wing rally-goers and the reasons why “white supremacist gang members” appeared to receive lenient treatment by police and prosecutors.

Sometime during the exchange, Outlaw reached for her phone.

The police chief could have texted Wheeler to ask him to interject and offer backup. Instead, public records obtained by The Oregonian show, Outlaw texted Eudaly.

The chief’s message: “You’re doing a great job.”

Outlaw and Eudaly arranged a tête-à-tête for later that night in the bar at an upscale restaurant steps from City Hall, according to their texts. While there, the chief told the commissioner her questioning hadn’t damaged their relationship, Eudaly recalled in an interview.

Portland Police Chief Danielle Outlaw, pictured on Aug. 10, 2017.LC- The Oregonian

Although Outlaw said her text to Eudaly was intended “to encourage and support her in her role as commissioner,” not to undermine Wheeler, who Outlaw said has her full backing, the exchange underscores the mayor’s struggle to keep key allies’ support given his performance during two bruising years in office.

Take Wheeler’s relationship with Deborah Kafoury, the Multnomah County chairwoman.

Kafoury said in an interview that it’s “really important” Portland’s mayor and Multnomah County’s executive have a good working relationship. Asked if she has that kind of link to Wheeler, Kafoury did not say yes.

“It's in the best interest of Multnomah County that the mayor is successful and the city is successful,” Kafoury said. "That is what I can say."

To get a sense of Wheeler’s performance halfway into his four-year term, The Oregonian/OregonLive spoke with the mayor, elected officials, current and former city executives, City Hall watchers and some of the friends and advisers who see Wheeler’s work up close. Many gave frank assessments on the condition their names not be used.

The interviews paint a picture of an intelligent, well-intentioned mayor who thinks quickly and enjoys diving into the subtleties of policy.

But they also reveal that many around Wheeler feel disappointment with his struggle to achieve the progressive agenda he sold to voters; dismay at an overworked and outmatched roster of mayoral aides; and frustration at Wheeler’s seeming inability to grapple effectively with civil unrest and Portland’s enduring homelessness crisis.

Significant campaign promises have fallen off the mayor’s to-do list or have been relegated to backburner status. Tellingly, most relate to police reform and homelessness.

Unfulfilled pledges include those to establish a landlord-tenant affairs office, end landlords’ ability to evict tenants without cause, dedicate increased property tax revenues to affordable housing, create an online database of landlords, expand the number of building inspectors, revamp the census of Portland’s homeless, pilot a city jobs program for people without homes, create a plan for moving homeless campers into shelters and eventually apartments, place body cameras on all police officers, demilitarize the officer corps, train all officers in anti-discrimination and de-escalation tactics and give subpoena power to the city’s police watchdog agency.

“I don’t think anybody recognized the seriousness of the homelessness problem, including Wheeler,” said Bob Stoll, a prominent attorney and informal adviser to the mayor. “But I do think he's worked extremely hard trying to get control of the situation.”

Wheeler’s former chief of staff, Maurice Henderson, said he believes the mayor still has a bold, hopeful vision for a more prosperous Portland. “The question is his energy and focus,” said Henderson, now a Trimet executive.

“If I were him, I would really try to focus on the top few issues that I could make a big difference on in the next two years,” one elected official said. “If the next two years look like the last two years, I don’t think the public is well-served.”

And the next two years may be even tougher. Wheeler may increasingly find himself in the minority at the city council dais after Commissioner-Elect Jo Ann Hardesty is sworn-in to replace retiring Commissioner Dan Saltzman in January.

Hardesty has not shied from criticizing the mayor and his bureaus, and his performance on police and housing policy in particular. She even called him “mayor what’s-his-name” during her Election Night victory speech (but later apologized for the comment as an unintended gaffe).

Commissioner-Elect Jo Ann Hardesty.Dave Killen

Then there is the mayor’s own office, which occupies most of third floor in City Hall. His overridingly young team of aides are constantly stretched thin, observers say.

One former bureau director said Wheeler is often hamstrung by senior members of his staff who “as a group don’t quite bring the right skillsets to the job.”

“They don't have enough experience being a professional bureaucrat,” the former director said. “You need people in the leadership offices who are going to push something forward and hold you accountable. They just don't have that.”

A current bureau director said disorganization in the mayor’s office is “very frustrating” to agency heads trying to achieve Wheeler’s mission.

“It’s like, who's responsible for what? What are the expectations? They kind of trip over themselves," the official said.

"I've always thought the mayor's office is understaffed,” said Alan Ferschweiler, president of the local firefighters’ union. He said Wheeler could use extra aides working specifically to tackle homelessness and civil unrest.

Eudaly, the city commissioner who was critical of Wheeler’s leadership on police issues, said she is sympathetic to some of his challenges. She cited his “extraordinary workload,” having taken on not only the police and housing bureaus into his portfolio but also the bureaus in charge of planning, permitting, finance and economic development.

“That’s a big issue right there,” Eudaly said.

Many who have worked with Wheeler take a sympathetic tone. The job of Portland mayor is unforgiving and its complexities are under-appreciated, they said. And they wish the public, and in particular the hecklers who constantly hound Wheeler during city council meetings, would give him a break.

Mayor Ted Wheeler speaks to protesters in 2017. The Oregonian/file

“It's been a rough two years for him,” Ferschweiler said. “I watch him at city council and I watch how people treat him and I find it inappropriate.”

“He’s under siege,” said the former bureau director. “Not only personally by protesters every Wednesday in council chambers, but publicly everyone is saying ‘Why aren't you dealing with this?’”

For his part, Wheeler said he is trying to stay forward-thinking.

“You have the luxury of focusing on the vision if you’re successful in managing the crises that come up. And as mayor, there’s a lot of crises,” Wheeler said. “I feel like we have been successful at balancing managing the issue of the day against the long-term vision.”

Asked how he is measuring his own performance, Wheeler said he has focused recently on the boring-but-important work of molding Portland’s vast bureaucracy into a nimble, 21st-century enterprise. He gave as an example the reforms he has begun applying to city budgeting, which aim to prod officials set long-term goals.

“A lot of what we do is process-oriented. You don’t end up with tangible outcomes,” Wheeler said.

The mayor continued: “I’m trying to keep the tangible outcomes in mind. But I don’t want to discount the fact that the work we do over here that’s sometimes invisible is leading to real improvements and outcomes.”

Pressed for what he would deem success on police and housing, Wheeler articulated modest goals. He said he would be satisfied if the $258 million Portland housing bond produces its promised 1,300 units. He’d also like to see the Broadway Corridor and other large planned developments break ground.

For the Police Bureau, Wheeler said he wants to see “more community engagement” and a police force that deals more compassionately with people who are mentally ill, homeless or drug addicted.

Though his term has been bleak at times, it is not without successes.

Wheeler touted as his wins the more than 600 affordable homes that have so far been built or planned under the Portland housing bond; his plan, dubbed Build Portland, to pay for infrastructure improvements including upgrades of roads and bridges; slow but steady progress to move Portland’s building permits system online; a fivefold decrease in 911 call wait times; the hiring of many new police officers and approval for a corps of unarmed support workers; and significant planning for development at OMSI, the Broadway Corridor, the Gateway business center and the South Waterfront, plus planning for a possible Major League Baseball team.

Mayor Ted Wheeler, seen leading a meeting of the Portland City Council.

Wheeler pins the brunt of the blame for his struggles on himself. But he also points to problems posed by the city’s commission-form of government, which affords the mayor almost no powers beyond those of an ordinary commissioner.

“I don’t think it’s the best model,” Wheeler said.

Outlaw, who until last year worked within a strong mayor-style government as deputy chief of the Oakland Police Department, said Portland’s way of governing makes being mayor exceptionally difficult.

“Expectations are placed upon him as if it was a strong mayor form of government, but it’s not,” Outlaw said. “People expect him to say and do all the things a strong mayor says and does, but they don’t recognize that he’s only one of five [commissioners].”

It’s unclear whether Wheeler will seek re-election. He has said the public should assume he will, but he has also been caught expressing disdain for the job.

Several advisers are crossing their fingers in the hopes he will go for another term, which would make him the first Portland mayor to file for re-election since Vera Katz in 1999.

“Frankly, I hope to God he does run again,” said Stoll, the attorney. “I think it’d be a tragedy to have another one-term mayor.”

Henderson, the former chief of staff, said perhaps what Portland needs most is consistent leadership.

“There’s a volatility that comes with constant change,” Henderson said. “I think we’re seeing that now.”

Wheeler is trudging ahead and trying to smile through it. Former Gov. John Kitzhaber, expressing frustration near the end of his second term, famously called Oregon “ungovernable.”

Wheeler isn’t going there.

“Yes, Portland is governable,” he said. “Yes, it’s challenging. It is what it is.”

– Gordon R. Friedman

GFriedman@Oregonian.com