This chapter explores the immediate postwar economic, political, and cultural environment of Milwaukee, a city where decades of stasis were compounded by a changing demographic that included suburban flight and an increasingly lower-income urban core. The long municipal governance by socialist Mayor Daniel Hoan (1916–1940) and the city's high levels of unionization had fostered a strong middle class from the early decades of the century through World War II. But far more than most industrialized Midwestern cities, Milwaukee had seen little modernization since the 1920s, with brewery industrialists and other business leaders markedly absent from contributing to citywide improvement, unlike their peers in cities such as Pittsburgh. By war's end, the necessity to meet the growing and evolving needs of city residents, and generate a solid financial base to do so, created a crisis atmosphere recognized by political leaders and private-sector actors alike.