This article explores the conditions for changing news media coverage of police brutality, focusing on the Chicago Tribune. Police have historically dominated news about policing, resulting in very limited coverage of wrongdoing. Following the murders of Fred Hampton and Mark Clark by Chicago Police officers, a racially and politically heterogenous coalition exposed the connection between police brutality and knowledge production. Activists developed a radical critique of police brutality’s role in sustaining an unequal social order and opened new possibilities for political solidarity. When longtime Chicago machine alderman Ralph Metcalfe challenged Mayor Richard J. Daley on the issue, “regular” Black Democrats came to join liberals and radicals in demanding change. The conflict generated by Metcalfe’s revolt provided both a justification and a set of questions for the Tribune’s investigative task force to engage. In a pathbreaking series of investigative reports on police brutality in 1973, the task force convincingly demonstrated the existence of widespread police brutality but also tamed its political significance with bureaucratic reform. The dilemmas of coalition politics that shaped this investigative reporting and the response to it continue to structure the choices faced by political movements seeking meaningful transformation today.