Background: This article examines the contemporary implications of the "Milliken v. Bradley" (1974) decision for educational inequality between school districts in U.S. metropolitan areas. We focus upon four metropolitan areas that were highly segregated in the 1970s but which met different fates in court: We first examine Detroit and Philadelphia, where plaintiffs sought but ultimately failed to obtain a metropolitan-wide desegregation ruling. We then examine St. Louis, where a court imposed a metropolitan desegregation remedy. We finally include Jefferson County, where the court order resulted in a merger of city and suburban schools. Objective: Through this comparative analysis we seek to tease out the effects of the ruling on patterns of inequity between urban and suburban school districts over time. We specifically examine how districts within these metro areas differed over time in terms of patterns of school segregation, fiscal resources, and academic performance. Research Design: We employed qualitative case study methodology. We purposively selected three case study districts within each of the four metro areas (total of 12 school districts) based on their contextual status in 1970, i.e., whether they were in each of these three categories: urban, segregated suburban, or affluent suburban. We compared them along three dimensions: patterns of segregation, academic outcomes, and fiscal resources. Conclusions: We found that the segregated and high poverty districts in the three metro areas where courts left districts intact (Detroit, Philadelphia, and St. Louis) have been, since "Milliken," increasingly hemmed in by their boundaries: struggling with growing concentrations of need, low resources to meet those needs, and as a result falling into fiscal and academic decline. In contrast, the maintenance of district boundaries by the courts has allowed the affluent suburbs in these contexts, over time, to benefit from a number of policies and practices that allowed them to accrue and protect advantage through exclusionary zoning policies and housing discrimination. Together, these policies have promoted and protected the affluence and advantage in each of these contexts, which has in turn attracted investment and allowed these districts to maintain strong financial standing over time. Our study suggests that socially constructed political boundaries, like school district boundary lines, by carving up political geography along the lines of race and class, can take on an active role in the reproduction of inequality.