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Following the 2007 Supreme Court decision in PICS and Meredith, this study investigated the efficacy of ensuing proxy policies replacing race-based student assignment strategies. Highlighting one intercity district—Chicago Public Schools—the author examined differences in racial composition at their elite, “selective enrollment” schools before and after such policies became unconstitutional. Using historical, document, and quantitative analysis of district/city records, scholarship, personal anecdotes, and news articles, findings show the rational transition to socioeconomic criteria are inadvertently resegregating Chicago’s top schools—in favor of whites. The author contends the Supreme Court’s decision to strike down race-based student assignment policies directly contributed to local policy changes for urban districts like Chicago, marking a distinct change in desegregation law and equity/access for minority youth.