PORTLAND, Ore. — On a cool September morning, a new volunteer outreach initiative designed to connect with unhoused Portlanders launched with speeches, backpacks of supplies, and promises of compassion. But only hours later, the same block that hosted the outreach saw a city-led sweep, underscoring the contradictions at the heart of Portland’s homelessness response.
Michelle and Penny
Among those first approached by outreach workers was Michelle, 45, who had pitched her beige tent a few days earlier along Northwest Fourth Avenue near Flanders. With her was Penny, the small brown dog she adopted after its previous owner died of an overdose.
“I haven’t been out on the streets like this for a minute,” Michelle said as she organized her belongings outside her tent just before 8 a.m. She has been cycling in and out of homelessness for years, staying at motels or with friends when possible.
Michelle quickly became a focal point of the day’s events—an emblem of both the promises and the limits of the city’s approach.
Mayor Wilson Rallies Volunteers
Earlier that morning, Mayor Keith Wilson greeted a crowd of volunteers, outreach staff, and nonprofit partners at CityTeam, a faith-based shelter in Old Town…