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First, this article explores begging and window washing as a form of radical commerce engaged in by an infamous homeless man in Auckland. Our approach brings to the fore the everyday spaces, tactics, and relationships that are central to the street life of Joshua. We consider how success as a breadwinner for Joshua’s street family not only engenders self-worth and a sense of belonging but also binds him to a street life that undermines his health. Second, we demonstrate the utility of the case as an essential tool for urban research in psychology. The case of Joshua is constructed from a series of informal, rapport-building conversations, a biographical interview through which Joshua offered an account of his life, and direct observations of Joshua window washing and begging. We also draw on a go-along interview where Joshua took us on a tour of his city, and four sets of photo-elicitation projects and …