This article describes the cultural characteristics of four elite African American high schools, initiated prior to Brown v. Board of Education, that produced outstanding graduates. Positive school culture characteristics examined were leadership, faculty, curriculum and instruction, student qualities, the environment, and internal and external relationships. The authors posed questions investigating how educators and alumni of Gary, Indiana's Theodore Roosevelt High School viewed the characteristics of its culture and how the culture compared to other elite African American high schools in the extant literature. Using surveys, archival information, and the research literature, the authors collected information describing the high school's distinctive features. Comparing the results of Roosevelt with the other exemplary high school cultures of Dunbar, Sumner, and Terrell, they reported these insights about their cultural characteristics: (a) high caliber and sustained leadership of individuals who cultivated positive school environments and created institutions that were a distinctive blend of school and community; (b) highly educated and qualified faculty members; (c) a rigorous and challenging curriculum emphasizing the preparation of students for higher education; (d) students who exhibited a strong sense of self-esteem, self-efficacy, and a rejection of the concept of inferiority; (e) a family-like environment that was welcoming, inclusive, and receptive to individuals from varied backgrounds that fostered a strong sense of pride and efficacy; and (f) a family climate experienced by internal and external stakeholders that created a sense of belonging and place.