This panel challenges Chicago’s fleeting place in the history of United States politics and culture during the 1960s. Though it remains the country’s third largest metropolitan center, the city’s best known moments from this pivotal decade occurred over only a three year period. Bookended by Dr. Martin Luther King, Jr.’s beleaguered efforts to promote “open” housing (1965-1966) and the more infamous “shoot to kill” orders by machine mayor Richard J. Daley in response to demonstrators at the 1968 Democratic National Convention and so-called “rioters” in poverty-stricken West Side wards, Chicago became a symbol for an era that began with redemptive promise but supposedly devolved into a moment of intractable urban decline. Yet the “tragic” denouement to hopeful mid-20th Century racial liberalism belies a far more complex and multifaceted story of social struggle from at least the 1940s through the 1970s. Papers on this panel provide specific case studies for how organized groups of Black activists had for decades been involved in a variety of understudied civic fields that complicate racial liberalism’s arc. The late 1960s featured religious leaders who channeled Black Power initiatives in their communities through educational missions as well as cultural workers interested in representations of African American heritage through public history who re-imagined the configuration and use of space in the city’s biggest public park. The period also featured the important agitations of Black patrolmen galvanized by increased police brutality and their own experiences with occupational discrimination and internal departmental surveillance, while new coalitions of housing activists continued to challenge the ever-shifting racial proscriptions of housing policies well into the 1970s. Such disparate initiatives helped provide the basis for broader movements that collectively reshaped the urban United States and helped usher in a later period of civic and multi-racial coalition-building.