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After five years on the street, one Portland man makes the journey from homeless to housed

Amid frustration over homelessness and tragic deaths of those trying to survive, one man offered a glimpse into the years-long journey he took to get off the street.

PORTLAND, Ore. — On a spring afternoon in Portland’s Old Town, the neighborhood is buzzing. A handful of tourists drag rolling suitcases down the street. The air smells of disinfectant as volunteers hose down a sidewalk.

On one corner, a woman lies on the ground in a sleeping bag eating a sandwich, then tosses the garbage into the street.

And then there’s Richard Winkowitsch. He’s sitting against a building, cigarette in one hand, colored pen in the other, sketch pad on his lap. He looks around at the dozens of tents lining the sidewalks and thinks of the one he lived in for five years; a life of homelessness he put behind him last week.

“The stabbing, shooting, stealing and all that, I got so tired of it,” said Winkowitsch. “Every single day. Stress, stress, stress, stress.”

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Winkowitsch said it’s hard to sleep on the streets with the fear of violence and theft always looming. During the day, he managed to get by, selling papers for Street Roots and helping out at Dixie Tavern on Northwest 3rd Avenue and Couch Street. On busy nights he still sets up cones outside the entertainment district mainstay and in return, Dixie staff give Winkowitsch food and a warm place to hang out in. 

“I love the people there,” said Winkowitsch. “They treat me right and I treat them with respect.”

Recently, Winkowitsch opened up to a Dixie staff member, telling him he was ready for a change.

“I said I need off the streets really bad so I can get my life back together,” he said.

That conversation got the ball rolling. In the days that followed, multiple people, agencies and nonprofits stepped in to help. On Sunday, Winkowitsch moved into the Wy'East Shelter on Northeast 122nd Avenue. It's run by Do Good Multnomah and funded by the Joint Office of Homeless Services. There, Winkowitsch has his own bed, access to a kitchen, bathroom and laundry facilities. He’s grateful for a safe place where he can lay his head at night.

“I sleep indoors, I can sleep wonderful,” said Winkowitsch, a smile across his face. “A good night’s sleep, no noise or nothing at all. Peaceful.”

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Winkowitsch still spends his days in Old Town. A quick MAX ride takes him right back to Northwest 3rd Avenue and the neighborhood he loves. He checks in on his friends and people he used to camp near.

“Mostly in my heart I love helping people out,” said Winkowitsch. “And if they don’t want help, I tried."

Suddenly, a woman crouched in a nearby doorway begins to yell and scream incoherently. It goes on for several minutes until Winkowitsch steps in.

“That’s Christy,” said Winkowitsch, excusing himself for a moment to bring the woman a cigarette. “When you give her a cigarette or a pop, she calms down ... if a person is struggling, help them out.”

Winkowitsch noted the woman he helped has struggled with methamphetamine for years. He said addiction is robbing many people's ability to advocate for themselves and decide that they are ready to leave the streets. Winkowitsch said he's been clean from hard drugs “for a while.”

“When you're high, you can't think what you're doing,” said Winkowitsch. “When you're off that stuff, you can think. I can think right now.”

Minutes later, Winkowitsch sees another familiar face. It’s Dan Lenzen, co-owner of the Dixie Tavern. He walks over to shake Winkowitsch’s hand.

“It just really makes me feel good about where he's going,” said Lenzen. “That narrative of ‘Nobody wants to [get off the street],’ that's not right... [We need] more outreach, more folks on the ground day and night — we can't just do it during the day because they don't work around daytime hours.”

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Many who decide they’re ready to leave the street still face obstacles. Getting basic things like proper identification, regular access to a phone and even the knowledge of what to do first can be difficult. For those helping Winkowitsch, the next goal is getting him into transitional housing.

According to the Joint Office of Homeless Services, partner programs in Multnomah County helped 1,780 people who were homeless get into housing between July and December, 2021.

Winkowitsch does his best to share the benefits of getting off the street with anyone who’ll listen. Not everyone is receptive to the idea; others are holding out hope that they'll be ready soon. As for Winkowitsch, he's now ready to get off the street every night.

“I leave early, about 10-10:30 and then go home,” said Winkowitsch. “It feels good to say that.”

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