This article addresses a crucial dimension of urban development: the recruitment of minority artists in the gentrification of space. The argument is that the production and exploitation of racial difference have underwritten the creative economy’s spurious claims to inclusion and diversity. Difference thus underwrites ideologies of developmental growth, proving a means of extracting monetary value and consolidating political power. The argument is grounded in an analysis of Kara Walker’s recent works—A Subtlety, or the Marvelous Sugar Baby (2014), an installation in Williamsburg, Brooklyn, and the Ruffneck Constructivist show (2014) in Philadelphia—and the debates they generated. A Subtlety thematized the gentrification of Williamsburg by putting it into relation with forms of humiliation associated with slavery. It also cast Walker, with some irony, as the scapegoat for related anxieties about complicity and success. The Ruffneck show, by contrast, imagined the decimated spaces of the midcentury welfare state to comprise an alternative ground for conceiving the racial origins of progress and thus for evaluating the epistemologies of contemporary liberalism. The article concludes with a discussion of social practice as it pertains to race in cities, situating Walker as a unique figure in this movement for having produced works that aggravate, rather than empower, her audience. Walker’s achievement has revealed the extent to which the debasement of others remains a central component of cultural production and liberal identification, today as in the past.