In late 1960s Chicago, radical black police officers opposed to police brutality created the Afro-American Patrolmen’s League (AAPL). This paper describes the political vision of the AAPL and that of the contemporaneous, path-breaking black television series Bird of the Iron Feather, which was inspired by the AAPL and created with AAPL members’ input. Both used their positions within white-dominated institutions to present black perspectives on white power. The AAPL and Bird also analyzed gangs, both black and white, as functional parts of a larger, white-dominated, urban "machine" political structure. Their analyses of structural racism, and their understanding of the diverse responses of black Americans living within such a system, uncovered the complexities of black urban life in the mid-twentieth century. Together, they stand as sophisticated expressions of a popular black power vision that eschewed romantic images of revolutionary resistance in favor of careful analysis of and resistance to personal and structural white violence.