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The relationship between segregation, black political experience, and civic culture in urban America is neither simple nor straightforward. This paper examines the development of a rich and varied black civic life in St. Louis during the first half of the twentieth century amid a climate of deepening racial hostility. As African-American migration accelerated, the city's white power structure mobilized for segregation. At the same time, African-Americans in St. Louis shifted political alliance to the Democratic Party, earlier than national trends. Black leaders capitalized on increasing numbers to seize the vote-getting power of the political machine, and used the Democratic Party to challenge old-line Republican ward bosses. Republican complicity in segregation, coupled with Democratic delivery of a major black teaching hospital, sealed the shift. Meanwhile, while segregation remained a constant feature of daily life, its application on the ground was uneven. African-American religious leaders, politicians, publishers, trade unionists, educators, and women's clubs took advantage of this uneven racial climate to construct a vibrant array of civic institutions. The clubs, churches, schools, hospitals, and media organs developed under Jim Crow nurtured a generation of African-Americans that would reject the segregationist framework of civic life in St. Louis.