Rarely do the public, community leaders, or policymakers engage the history of structural racialization. Despite this lack of public awareness, a large body of literature illustrates the importance of urban development history as a mechanism of upholding the philosophy of segregation upheld by Plessy v. Ferguson. The history of structural racialization in development is fundamental to understanding contemporary challenges such as segregation, concentrated poverty, and racial disparities. The following case study explores two Ohio community-based initiatives (in Cleveland and Columbus) that used historical analysis of racial discrimination in development practices as the focus of a community engagement process. Surveys, participant observations, and interviews document the outcomes, benefits, and impacts associated with engaging stakeholders using historical records of discrimination to inform contemporary policymaking. The study lends support to the importance of public engagement processes to uncover the various long-term ramifications of the "separate but equal" doctrine of Plessy.