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Recent data suggest that students of color continue to lag behind their White peers on certain academic performance indicators. Moreover, the literature reveals that Black students in urban schools face various barriers that may lead to poor academic outcomes. Despite these challenges, there is evidence that certain leadership approaches can make a considerable impact on the achievement of Black students in urban environments. Thus, this book chapter reviews the effective approaches of successful Black principals in these schools. In addition, using Lomotey's (1993) framework of the leader as a bureaucrat-administrator and ethno-humanist, we present a vignette of Mr. Jesse Franklin, the principal of an urban high school in the Midwest. Mr. Franklin was able to effectively balance his role as both a bureaucrat-administrator and ethno-humanist, and during his tenure as principal, student academic achievement increased. However, not everyone appreciated Mr. Franklin's approach and leadership style, and as a result, he was eventually dismissed as principal.