Tracing the history of the downtown lodging house districts where marginally housed youth regularly lived beginning in the late 1800s, I focus on San Francisco’s Tenderloin from the 1950s to the 2010s. Drawing on archival, ethnographic, and oral history research, I explore the social trauma inflicted on street youth and the ways they have worked, collectively and creatively, to reframe and reinterpret those brutal realities. I focus on four world-making practices: kinship networks my informants call “street families,” which resemble the moral economies common among people with severely limited resources; syncretic religious formations I call “street churches,” which are often based on a streetwise, gothic Catholicism; storytelling strategies that enabled youth to secure employment in the district’s vice and bar economies and, at times, to reinterpret the abuse from which they were running; and migratory circuits that connected far-flung tenderloin districts across the country and the people who traversed them, all the while fostering alternative socialities, cooperative economies, and novel forms of mutual aid.