An established literature describes political incorporation as the extent to which a group has achieved significant representation and influence in political decision-making (Browning, Marshall, and Tabb 1984; Bobo and Gilliam 1990). Political incorporation theory is largely developed through studies of the elections of black mayors in large central cities. Because central cities tend to share characteristics, and because there is little variation in the sociopolitical context of these cities, political incorporation theory cannot account for the degree to which context matters to the achievement of incorporation. This research is shaped by John Mollenkopf’s (1986) use of an anomalous New York City to convey the point that the specificities of place matter more to political incorporation than Browning, Marshall, and Tabb (1984) initially recognized. What are the different paths that cities take toward incorporation? How do context-related characteristics determine the path that each city takes? This research uses a comparative case study of two Chicago suburbs—Evanston and Waukegan—to deepen our knowledge of the process of political incorporation. Using qualitative methods—including interviews and focus groups with residents, political activists, civil rights organization members, educators, and political officials—this research focuses on three aspects of the sociopolitical context: black civic fabric, political leadership, and racial dynamics. Despite the demographic similarities between Evanston and Waukegan, both cities have vastly different sociopolitical contexts, opposite paths to incorporation, and different resulting levels of black political incorporation. This dissertation reveals that the achievement of political incorporation is context-specific. The path toward incorporation in both cities was continually shaped by the local sociopolitical context, and numerical strength within the black population alone was insufficient for overcoming context-related obstacles to incorporation. While parts of the sociopolitical context that are external to the black community shape the path to political incorporation significantly more than the current literature suggests, this dissertation also concludes that factors internal to the black community—like racial solidarity and a closely-knit black civic fabric—have a greater ability to overcome sociopolitical contexts that are oppositional to political incorporation than previously expected.