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Historical analyses of gender and racial trends for advanced degree educational attainment have revealed a striking underrepresentation of Black males. Grounded in social cognitive theory, the purpose of this study was to explore critical factors that promoted academic success among Black males who held at least one advanced degree and were currently serving as leaders within educational institutions. A phenomenological qualitative research design was employed, and data were collected from observations, individual interviews, and correspondence between the lead researcher and participants. Data were analyzed using three levels of coding and constant comparative techniques, which generated four themes identifying favorable critical factors that promoted educational attainment of advanced degrees among participants. Limitations and areas for further research were also described.