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The purpose of this study is to examine the principal leadership at an urban high school where reform has occurred in concert with community development and increased school-community partnerships. To achieve this purpose, this study addresses the research question: What actions do urban high school principals take to support high school reform along with community development? To conceptually frame this study, this paper uses Yosso's community cultural wealth framework. Data analysis was conducted using the constant comparative method and the conceptual framework that shaped this study. This study draws on 11 in-depth interviews, 8 school and community observations, and detailed field notes. Finally, the study concludes with implications for leadership preparation and future research.