Zach Brothers is a laid-back guy. He’ll tell you as much, if you ask, but his perfect day would be a laid-back day, relaxing, maybe fishing or playing games, somewhere with a nice view.
Brothers, who also goes by the name Cherokee, is originally from Michigan. He came to the Pacific Northwest a few years ago to live with family in the area and, when he wasn’t able to stay with them anymore, came to Portland. That was about four years ago.
“I was homeless once before in Michigan, and it’s different. (There’s) not a whole lot of resources out there,” he said. “There wasn’t anywhere near as many places as we have out here.”
A few months ago, Brothers was looking for work in Portland, but it was tough to come by — especially because his identification and Social Security card had been stolen. Word of mouth brought him to Street Roots.
“It’s been really good,” Brothers said. “There’s a lot of sense of community out here, especially for the vendors.”
Brothers is good friends with another Street Roots vendor, Bizmati Heflin. They play Dungeons and Dragons together at the Portland State University library. They use milestones and achievements to determine character level ups, as opposed to the traditional leveling up mechanic of experience points. That can make the game more challenging, but also more rewarding.
“We’re about three seconds in and we’ve already got a kingdom,” Brothers said of their current campaign.
The community of vendors at Street Roots was also a support system to lean on when Brothers lost his dog Hel (named after the Norse goddess of the underworld) early this year.
He was staying at a shelter on Northeast Killingsworth Street, near Interstate 5, when he got a call from the Oregon Department of Transportation. Hel had been hit and killed by a car on the interstate. She was just under six years old.
“She was probably just trying to get back home (to the shelter),” he said. “She was the sweetest little baby there ever was.”
Brothers isn’t just part of the Street Roots vendor community — he’s also an advocate for expanding that community.
“Any time I see people panhandle, I tell them to come here. It’s not much, but it’s honest work,” he said.
Sometimes he’ll sell a ton of papers in a day. Sometimes just a few.
“Either way, I’m putting the work in,” he said. “Most of the time it’s just, ‘Good morning, or good afternoon, can I interest you in Street Roots for a dollar?’ And if they do, thank you, and enjoy your day.”
You can support Brothers through @StreetRoots Venmo by entering his name and badge number (#1511) in the memo.
This article appears in March 18, 2026.