Not articulated by school reformers are the obstacles created by the historical mismatch between the needs of African American communities and the limited opportunities from their local schools. The Chicago context is the focal point of this discussion because the school system is currently undergoing its third wave of school reform in 10 years and the schools struggling the most through this change process are located in African American neighborhoods. By drawing on and integrating existing literature concerning Chicago's communities and schools, this article reviews the historical interplay between urban processes and school capacity in order to critique the current task at hand for school reformers in Chicago. Historical sets of actions have segregated African Americans into resource-deprived communities. The long-term effects of community resource deprivation make it challenging for any local institution to provide services at the level needed for families with diminished life trajectories. Schools are one of the few community institutions parents rely on to provide opportunities for their children. However, the same resource deprivation that has affected families and communities undermines the ability of schools to organize effectively to meet students' academic demands. As we consider the current wealth of school reforms, what is missing from the dialogue is a concentrated focus on how urban processes and school capacity are intertwined. The intent of this article is to understand this connection and provide a framework to help schools provide educational support and services by considering their own community's social and economic histories. In this school reform era, we have yet to explore the challenges that historical trends in community conditions pose to local schools. While the effective schools literature has informed us of the necessary ingredients for school improvement to occur (see Bryk et al., 1998; Comer, 1993; Meier, 1995; Slavin, Madden, Dolan, & Wasik, 1996), the social and economic transformations that have occurred in many central cities are often used as descriptors versus central considerations that complicate the school improvement process. In turn, the literature linking social and economic trends to schooling inequities does not explore the manner in which these trends penetrate the educational processes occurring within the school building (see Anyon, 1997; Mirel, 1993). This work bridges the gap by examining social and economic community trends and their concomitant effects on schools as well as the cumulative effects of these urban processes on modern day school capacity. The Chicago context is used as the focal point of this paper because the city's social and economic transitions are well documented (see Drake & Cayton, 1945; Duncan & Duncan, 1957; Frazier, 1951; Massey & Denton, 1993; Wilson, 1987, 1996), and similar to other cities that experienced African American population growth during the Great Black Migration (see Anyon, 1997; Franklin, 1979; Mirel, 1993; Mohraz, 1979). Additionally, the city has a history of controversial urban policies and practices, designed to manage the demographic changes that occurred in the city (see Drake & Cayton, 1945; Frazier, 1951; Halpern, 1995; Hirsch, 1983; Lemann, 1991). Chicago is also a city struggling to change its public schools. The school system is currently undergoing its third wave of school reform (1991-1996; 1996-2001; 2001-present) in 10 years (Bryk et al., 1998; Hess, 1999).' Interestingly, the schools that are struggling in the change process happen to be in the city's most disadvantaged neighborhoods (Bryk et al., 1998; Designs for Change, 1985). From a policy perspective, understanding this link between the social and economic transitions of communities and school capacity can shift the school reform conversation from one focused exclusively on the school building. Instead, aligning trends in community conditions and school capacity should illuminate the need to take a holistic approach to school improvement by also addressing students' noninstructional needs. …