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Midwestern towns have experienced economic stagnation in recent years, creating political and social challenges. To better understand them, I examine Mount Vernon’s industrial development from 1830 to the present and the organizational structures of its three largest companies – Ariel, Coopers, and Pittsburgh Plate Glass (PPG). This analysis reveals repeating patterns of economic dislocation and readjustment. I argue that this alteration was the result of two broad dynamics. First, the local economy integrated into larger and more distant markets; firms sought to meet national and global, rather than just local demand. Second, the changing organizational structures of the local companies shaped their local commitments. Ariel retained private ownership and a local focus, while Coopers and PPG became publicly traded, sprawling conglomerates that lost touch with the town. From this analysis, an important lesson emerged: the trade-offs evident in economic and social life. While firms’ structural changes generated greater economic growth, they also introduced greater economic and social instability.