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Credit: Photo by Cole Merkel

On the chilly afternoon when we spoke, Tony Boone was about to go to Canby for three days where he has a job making clothes at an old friend’s house. He doesn’t think of it as work though.

“It’s a vacation,” he tells me. Over the next few days, as Portland freezes to the bone and the snow piles up, I wonder if Tony knew something I don’t. He talks again and again about the mix of luck, vigilance and positivity that has enabled him to survive on the streets.

“I’ve been homeless before, and I’ve gotten off the streets before,” Boone says. “So I try to keep a positive attitude every day and just keep pluggin’ along.”

He had just found out earlier in the day that one of his daughters will be soon moving to Portland from Wisconsin. “I’ve got good things on the horizon.”

Tony was born in Albany, Oregon, but followed his father’s Marine postings all over the country — Oregon to Virginia to California to Tennessee — before his parents divorced and he settled with his mother in Appleton, Wisc. He had three daughters there and was in and out of prison by his 20s.

“I decided something’s gotta change, I gotta get outta here. I promised my daughter I wouldn’t go back to prison, so I can’t go back to prison.”

He caught a bus to Los Angeles and spent a few years hitchhiking up and down the coast. He estimates that he made the round trip between Eugene and San Diego more than 50 times. Eventually, in the winter of 1995, he ended up in Portland and it became his hometown.

For the most part he maintains a positive outlook despite the stress and loneliness that can be a large part of homeless life in the city. He began selling Street Roots last summer, after he broke his leg and lost his job and home. He was flying signs when another vendor told him he should try selling the paper. He feels lucky to have stumbled on his current turf — Zupan’s Market at Southeast 34th Avenue and Belmont Street — and was able to establish himself there.

“I got my bike, the trailer, this jacket, all from customers,” he tells me, pointing out his gear in front of the Street Roots office. He credits his easy approach for his success. “I try to talk to people, say, ‘Hey, how ya doin’, but without actually asking them if they want a paper. It seems to work out fine.”

When I ask him if he has anything he’d like to add, Tony says “I need a drum. That’s the thing I miss the most. I’ve been playing the drums since my earliest memory. I can play any kind of drum.” His last drum, a Remo Signature Series djembe, was stolen while he slept. He laughs at the nerve of the thief who crept up and cut the strap attaching the drum to his backpack, and then shrugs it off. “But, you know, I’m a heavy sleeper.”

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