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Homelessness was the issue that helped sweep Portland Mayor Ted Wheeler into office.

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When Wheeler announced his campaign, he presented himself as an alternative to then-Mayor Charlie Hales, whose decision to allow public camping led to a spike in tent cities and public backlash.

Wheeler pledged that under his watch, every person sleeping on Portland’s streets would have the option of heading inside.

“We have a stark choice,” he said at the time. “Do we want more promises on helping the homeless get into transitional housing and get the help they need, or do we want progress?”

Three years later, Wheeler has not kept that promise. The city and county have added a few hundred beds under his administration. But the increase in shelter space has not kept up with the homelessness crisis. The 2019 Point in Time count found 2,037 people sleeping on sidewalks, in cars or in tents on any given night.

Portland Mayor Ted Wheeler has increased funding for crews that force homeless people to move every couple of weeks and clean up their campsites. Kaylee Domzalski / OPB

Wheeler said he’s come to understand that solving homelessness requires more than emergency beds.

“The evolution in thinking on my part, and also nationally, is that we have to address the underlying causes of homelessness for the chronically homeless population,” he said in a recent interview.

That means making sure outreach workers are connecting people on the street with the specific services they need to end their homelessness, such as access to housing, addiction treatment or help living with a disability. To that end, the mayor has increased the city’s funding for shelter and services from $25 million when he took office to $32 million this year.

Wheeler said that while some Portlanders expect a compassionate response to homelessness from their mayor, others are primarily concerned about what he calls livability impacts and public safety.

“The litter, the needles, the encampments and the like: All of these are legitimate concerns,” he said.

Wheeler has also increased funding for the crews that force homeless people to move every couple of weeks and clean up their campsites. The mayor’s office said those crews have removed 375 tons of trash and 22,000 needles this year.

Related: Portland Tourists Will Now Help Pay For Homeless Services

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Portland Commissioner Nick Fish credits Wheeler for working closely with other City Council members on policies to prevent homelessness, including Commissioner Chloe Eudaly’s sweeping package of legal protections for renters and Fish's own effort to pay for 2,000 new units of housing for people who need supportive services.

“In order to be successful in our form of government, you have to work well with others,” Fish said. “I don’t think Ted gets enough credit as a collaborative leader who has helped move this council forward to make real progress on homelessness.”

But where Fish sees a leader willing to learn on the job and collaborate, others are less impressed. Real estate developer Homer Williams donated to Wheeler's first campaign. Three years into Wheeler's tenure, Williams said he worries that the mayor and other elected officials don't treat homelessness with the urgency they'd bring to other humanitarian crises.

“If we had an earthquake tomorrow, and we had 10,000 or 15,000 people on the streets, we would have them housed in tents, with bathrooms, with food, with showers, within a month,” said Williams, who chairs the private nonprofit Harbor of Hope, which is working to develop shelters that connect people to services. He opened the first in the Pearl District with funding from private donors, Multnomah County and the city.

In spite of their partnership, Williams struggles to describe the mayor’s vision on homelessness. When asked whether Wheeler has done anything to move the needle on the crisis, Williams paused for around 10 seconds before asking for more time to think.

“I think he’s really now coming to grips with the magnitude of the problem,” he said after several minutes. “And he’s willing to make it his No. 1 priority.”

OPB spoke with four other local elected leaders and activists who work on housing and homelessness. All criticized the mayor’s approach, but none were willing to go on the record. They said it can be hard to get his office to focus on homelessness, to prioritize funding for it or to take action on specific policies.

Mayor Ted Wheeler received the demands of the student activists after they marched to Terry Shrunk Plaza across from City Hall. Cheyenne Thorpe / OPB

Fish said he thinks the mayor’s problem is his communication style, rather than the substance of his work.

“Is he our best orator? No. But at the end of the day, is he making steady progress in addressing what he says was his No. 1 priority?” Fish said. “The answer is demonstrably yes.”

Wheeler said that if he gets another term, he will focus on long-term solutions to homelessness, such as subsidized housing for people who face the biggest challenges to get off the streets.

“We’re making good headway, but we need to scale it up,” he said.

Scaling up supportive housing will take millions of dollars regional governments don’t currently have, though a group of business leaders, nonprofit providers and elected officials is working on a ballot measure that could raise hundreds of millions annually for homeless services.

The measure could be on the November 2020 ballot. So could Wheeler if a challenger pushes him to a runoff.

He promises he’ll campaign for the homeless services package.

“It will be the easiest ask I’ve ever made,” he said. “This is the No. 1 issue facing our community, full stop.”

Correction: This story originally said that Mayor Ted Wheeler had not yet signed onto a letter supporting the Here Together homelessness effort. He endorsed the letter late last month.