In 1983, black Chicagoans elected Harold Washington as the city’s first black mayor. In the process, they overthrew the white Democratic machine and its regime of “plantation politics.” This book details the long-term development of black Chicago’s political culture, beginning in the 1930s, that both made a political insurrection possible in the right context, and informed Mayor Washington’s liberal, interracial, democratic vision of urban governance. Building upon recent studies of the “Long Civil Rights Movement,” which focus largely on a black radical tradition, this book recovers the history of a long tradition of black liberalism at the ground level. Men and women, largely unsung, made history by engaging with – rather than rejecting – the institutions and ambitions of urban life, and by connecting their individual aspirations to the collective interests of the race. They maintained popular critiques of overlapping systems of race, class, and gender inequality and developed local crucibles of black power that made pragmatic reform possible and set the stage for Washington’s victory and – in surprising ways – even the ascendance of Barack and Michelle Obama. The tragedies of incomplete and uneven racial progress are undeniable. Yet, in struggles for decent housing, good jobs, and political power over a half a century people worked to overcome racial segregation and inequality in everyday life. Consequently, this study shows that the image of the Second Great Migration as an inexorably tragic event is no longer tenable, while it also integrates the story of black urban politics into the deeply ambiguous history of American liberalism.