Jaqualynn Dettmer crouched low in front of one of the two tents set up under the Interstate 205 onramp at Southeast Woodstock Boulevard. Both were covered in tarps against the early December chill. Another tarp covered a collection of bicycles.

“Do you want a sandwich?” Dettmer asked after greeting the people staying inside the tent. They did. Dettmer, the leader of the Salvation Army’s mobile outreach team, gestured to one of her colleagues, who brought over several sack lunches.

This is the work of an outreach team, of which there are now dozens across the Portland area, funded almost entirely by money from the Metro homeless services tax. The tax on high-income earners and businesses has funneled nearly $1 billion into homeless services in Multnomah, Washington and Clackamas counties since 2021, fundamentally altering what services local governments can provide. That tax could be up for renewal on the November ballot.

Between them, the three counties have budgeted $19.5 million in homeless services tax revenue for direct outreach to people living outside in the current fiscal year. Research has consistently shown building relationships with people living outside can lead to a reduction in homelessness. Effective outreach that starts with handing out survival supplies and ends with a connection to housing services is among the key homelessness reduction strategies recommended by the U.S. Interagency Council on Homelessness.

Several local politicians, including former Portland Mayor Ted Wheeler and current Mayor Keith Wilson, have expressed concerns about outreach workers handing out supplies, especially tents and tarps. Wilson is adamant that offering people a safe place to sleep is kinder than giving them supplies to remain outside.

Others have criticized the practice too. In 2023, Portland agreed to clear more tents from sidewalks and extend its ban on city employees handing out tents and tarps to settle a lawsuit brought by 10 residents who have, or cared for people with, physical disabilities.

County outreach teams continue to hand out tents and tarps when weather conditions become severe. But most of the supplies they hand out are basic human necessities, like food, said Kristi DeLaGarza, who oversees the Salvation Army’s mobile outreach program.

DeLaGarza said their work is necessary. Hundreds of beds have been added to the region’s shelter system using revenue from the same tax that pays for outreach, but there are still not enough to go around. That’s especially true in Multnomah County where nearly 6,000 people live outside, according to an August estimate from the county obtained by The Oregonian/OregonLive.

“I’ve had lots of people say to me that we’re just enabling people to live this fringe lifestyle, but I think it’s important to do what we can until we can do more,” DeLaGarza said. “We’re not creating a situation where people thrive living in a tent. We’re helping people survive.”

For outreach workers, the wins can be scarce. Expecting to show up and immediately solve everyone’s problems would be a mistake, members of the Salvation Army’s mobile outreach team agreed.

A lot of the time it’s just about “treating people with dignity,” team member Charles Boykins said. “You got to have that inside you to do this work.”

Like all county-funded outreach workers, Boykins enters data on the interactions he has with the people he meets after every trip. But so far, none of that data is public. Multnomah County officials plan to release a detailed data set on the demographics of the local homeless population in the next two months. That data, known as a “by name list,” is also supposed to capture how well various efforts, including street outreach, are working to help people find housing, treatment and other needed resources.

Leaders in Clackamas County are also beginning to track how effective their outreach efforts are. In the final six months of 2024, Clackamas County outreach teams contacted 549 people, 440 of whom are now “engaged in a plan to address their housing situation,” county spokesperson Claire Okeke wrote in an email.

There were no formal outreach teams in either Clackamas or Washington counties before the homeless services tax revenue became available. Both have since invested millions of dollars in their outreach efforts.

“Coordinated and integrated outreach workers are critical to our homeless system of care,” Washington County Assistant Director of Homelessness Jes Larson wrote in an email to The Oregonian/OregonLive. “They are our ‘front door,’ the ‘first hello,’ and the helping hands that connect people who’ve long been left outside back inside and reconnected to their community so they find stability again.”

Since July 1, Washington County outreach teams have helped 204 people move into shelter or housing, according to Nicole Stingh, a manager in the county’s homeless services division.

The Salvation Army’s four-person Multnomah County outreach team, one of many in the county, began going out in a customized supply bus during spring 2024, DeLaGarza said. The program has an annual budget of $523,745, entirely funded by the homeless services tax, according to the Salvation Army. The nonprofit plans to launch a second mobile team soon.

Back on Woodstock, Dettmer and her two colleagues crossed the street to a camp directly under the interstate, set in a field of huge boulders placed there by government officials to deter camping. A man in red plaid walked toward them with a friendly wave.

“These are my people,” he said, introducing himself as Kenneth Van Alstine. He said he wasn’t staying at the camp, just visiting friends. “Being out here is a level of freedom that is intoxicating. It’s alluring to a lot of people.”

Van Alstine, 34, said he was recently out of jail and sober for the first time in a long time. He was living inside with his partner. And he was ready to find a job and settle down. He wanted to work for Rapid Response, the city contractor responsible for cleaning up tent camps and hazardous waste around Portland.

“I feel like a traitor doing it,” he said. But he said the Rapid Response workers he’d met were like him – previously unhoused or incarcerated – and they weren’t bad guys. Plus, he’d start at $18 an hour, better than he thought he could expect for most jobs with his record.

Besides, Van Alstine said, it wasn’t fun being outside anymore. Heroin had been one thing. Heroin had been fun. But fentanyl was not. He said that when using fentanyl he had to get high so frequently to avoid the let down that it took away any ability to connect with others or even to maintain a sense of self.

Fentanyl swept into Oregon during the pandemic and the storm has not yet abated. In 2023, 1,336 Oregonians died of a fentanyl overdose, according to the U.S. Centers for Disease Control and Prevention, a sixfold increase from 2020. People living outside were especially vulnerable. Of the 456 homeless people who died on Portland’s streets in 2023, nearly two thirds died of an overdose. Most of those deaths involved fentanyl.

With cars rushing by noisily overhead, Dettmer settled into conversation with a young woman with long dark hair. She told Dettmer she was ready to get clean. She just wasn’t sure if now was a good time because she wanted to be easy to find when her boyfriend got out of prison. That could be any day and if she started treatment, what if he couldn’t find her when he got out?

Dettmer, who grew up with six siblings in a tiny off-the-grid house, listened to the young woman without judgement. Then she pointed out that the boyfriend would be sober when he was released since he’d had to detox in jail. Maybe, she suggested, now would be a good time to get treatment, for which there can be a long wait list. The young woman agreed and accepted a card with information about who to call.

Dettmer knows how hard it is for people dealing with substance use disorder to seek and find help. She has a brother who has lived outside in Seattle for five years. He has schizophrenia, she said, and is addicted to drugs. Dettmer is deeply religious and said she sees her work as a way to show God’s love to everyone.

“God is good,” Dettmer said. “He’s good all the time. We just have to create the space to look at the light.”

Dettmer left the Salvation Army in January. She told KGW in a late January interview that the Salvation Army’s opening of 200 new overnight-only shelter beds at the city and county’s behest had put too much pressure on workers.

“I think it doesn’t really cultivate a healthy environment for anyone involved,” she told KGW.

Dettmer did not respond to a message from The Oregonian/OregonLive on Friday. The Salvation Army declined to share details about her departure.

Turnover in the homeless services workforce is an ongoing issue. More than half of employees at county-funded service agencies who responded to a 2022 survey said they were somewhat or very likely to look for a new job during the next year. And only 31% of the same group said they felt their compensation allowed them to take care of their basic needs. In the past fiscal year, the county dedicated $10 million in workforce retention grants to service providers. County officials are also starting work to “re-base” contracts so that workers are paid high enough wages to stay.

The Salvation Army now pays new outreach workers $27 an hour.

Many outreach workers bring relevant life experience to the work. John Goertzen, another Salvation Army outreach worker, has himself been homeless and struggled with addiction. A veteran who served in Operation Desert Thunder in the mid-1990s, Goertzen landed in the Salvation Army’s transitional housing units in Oregon City after he was evicted. He decided he was ready for more stability and returned to the peer support work he’d trained for as a way to help fellow veterans.

“Being out here builds more resilience,” Goertzen said. “It’s a reminder of where you could have been.”

Under the highway, Jalen Warren said he and his companions had been there for about a week. They had built a fire pit, complete with a tarp to block the wind from blowing out the flames. Warren, 24, cracked some eggs into a cast iron pan and cooked them over the fire to demonstrate how he used the makeshift kitchen.

“This is my life,” Warren said. “The people who stay with me are like my family.”

Warren, who wore his long hair pulled back into a low ponytail, said he grew up in Lebanon, about an hour and a half south of Portland. He said he came to the city after dropping out during his junior year of high school in Sweet Home. He was hoping to find his mom, who hadn’t been a big part of his childhood, but when he did she was couch surfing and didn’t have a place for him to stay. He’s lived outside since 2020.

He collects cans to make money or designs “fly signs” on spare pieces of cardboard to collect donations when he’s low on cash.

“The older cats, they make a lot,” he said of the signs. It’s important to put something different on your sign and to find a good spot to sit, he said. He’s used: “Everything you provide is a blessing” and “Thank you for your kindness, anything helps.”

Many of the donations he gets come from people he thinks are immigrants. He said he’s always grateful for “someone who has that in their heart.” A few nights before, he’d pulled in enough to buy teriyaki for dinner. It was hot.

Warren said he had a phone number for Urban Alchemy, the service provider that runs three of the city’s village-style shelters with private sleeping pods. His phone usually wasn’t charged though, he said. And he was worried that if he moved into shelter or housing he’d lose his street family. The Salvation Army outreach workers urged him to consider making the call, but they didn’t push too hard.

As Dettmer, Goertzen and Boykins left the campsite and headed back to their van, several other people approached them asking if they had hand warmers, blankets, food. They did. They handed out everything that was requested.

Boykins and Goertzen went back to the camp about a month after the December visit. They said it was empty of both tents and people.

Editor’s note: Since voters passed the Metro homeless services tax in 2020, nearly a billion dollars have flowed into Portland-area counties to help people without a home. Five years later, people are still becoming homeless faster than counties can house them.

Voters may soon have to choose whether to approve a measure that would renew, modify and extend the homeless services tax, possibly until 2050. This is the first in an occasional series by The Oregonian/Oregon Live that will highlight some of the many programs the tax funds.

Lillian Mongeau Hughes covers homelessness and mental health for The Oregonian. Email her with tips or questions at lmhughes@oregonian.com. Or follow her on Bluesky @lmonghughes.bsky.social or X at @lrmongeau.

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