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Street Roots vendor profile | Richard Winkowitsch acts with kindness

Street Roots
Richard is a listener and tries to focus on the positive
by Dylan Jefferies | 2 Mar 2022

Richard Winkowitsch is passionate about helping others. Despite experiencing houselessness himself, he is always looking out for his neighbors and making sure they have what they need. He likes helping people get back on their feet.

“I’ve got a kind heart,” he said. “I love helping people out in the community. It’s what I do. It brings me joy.”

An Iowa native who recently came to Portland, Richard has sold Street Roots for a few months. He decided to become a vendor shortly after learning about Street Roots. He needed help and wanted an opportunity to help others, too.

“Everybody in Portland loves Street Roots,” he said. “There are good people here. It’s a good place to be. It’s a good place to help out.”

He volunteers at Street Roots’ office because he enjoys getting to know people in the community. Plus, by volunteering, he’s able to pick up extra papers to sell.

He sells them at the Safeway downtown at 1303 NW Lovejoy St.

“They enjoy having someone selling Street Roots there,” he said.

His customers are often excited to see him, he said, and he always treats people with respect and tells them to have a good day. One day, a man became upset with Richard for selling the paper, but Richard responded with kindness. Later, the man returned and apologized. Now, he’s one of Richard’s regular customers.

“When people are ornery, I just smile and tell them to have a nice day,” he said.

While he enjoys helping others, Richard has struggles of his own. He currently lives in a tent in Old Town, and he’s tired of being in the cold. He worries about shootings. He wants to find a caseworker who can help connect him with resources, and he hopes to find an apartment soon.

“I just need some help so I can get back on my feet again,” he said.

When Richard becomes frustrated or irritated by his situation, he likes to ride the MAX out to the airport. Watching the planes come and go relaxes him.

“I go sit out there for a couple hours and come back and start over fresh,” he said.

Being near water is another thing that gives Richard solace. When he was a kid, he used to go fishing with his dad. Those times are some of his fondest memories, and he dreams of fishing again one day — standing in the river beneath a canopy of trees, somewhere deep in nature.

“We’d catch the biggest fish,” Richard said, reflecting on those times with his dad in Iowa. “Black Crappie, Bluegill, Bullheads, Walleye, Bass, you name it. We used to catch carp, too, and those suckers are huge. I once caught a 40-pound carp a long time ago. I was a kid, maybe 13 years old. I was having a hard time getting it in, so my dad had to help me out. Yep, me and my dad used to stick together fishing. We were always camping. I love the outdoors.”

Richard loves meeting new people. It’s part of why he enjoys volunteering with Street Roots. When he meets people who are struggling, he gives them a cup of coffee. He listens to them. He tries to get them to focus on the positive.

One piece of advice Richard likes to give people is to keep a to-do list that includes even simple tasks. Every day, his to-do list reads: “wake up, drink coffee, eat breakfast, go to Street Roots.”

“Check, check, check,” he said. “If you forget everything, you skip everything.”

While things aren’t always easy, Richard enjoys life. Helping others gives him purpose, he said. He looks forward to getting back on his feet soon, finding a caseworker, an apartment and hopefully some work.

“I enjoy work, and I am a good worker,” he said. “I used to do construction, farm work, carpeting, things like that. Like my dad used to say: ‘You’ve got to work hard in life.’”


Street Roots is an award-winning weekly publication focusing on economic, environmental and social justice issues. The newspaper is sold in Portland, Oregon, by people experiencing homelessness and/or extreme poverty as means of earning an income with dignity. Street Roots newspaper operates independently of Street Roots advocacy and is a part of the Street Roots organization. Learn more about Street Roots. Support your community newspaper by making a one-time or recurring gift today.
© 2022 Street Roots. All rights reserved.  | To request permission to reuse content, email editor@streetroots.org or call 503-228-5657, ext. 404
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