Using a wide array of official and unofficial data spanning two decades in the neighborhoods of Chicago, we explore connections between legal cynicism, the electoral regime of Mayor Richard M. Daley, and citizen calls for police assistance and police reports of drug crime. We find that the disproportionate concentration of legal cynicism about law enforcement in African American neighborhoods played a prominent and insufficiently understood role in building opposition to Mayor Daley’s political machine. This race linked legal cynicism was grounded in neighborhood concerns about effective prevention of and protection from drug crime. The more punitive than preventative and protective approach to drug law enforcement that characterized the politics of the Daley crime machine contributed to a legacy that foreshadowed the growing and ultimately explosive demands for new mechanisms of police accountability in Chicago.