Black males like other students face struggles persisting in college; however, in predominantly White colleges they must deal with issues of race and cultural differences. The purpose of this study was to explore how Charismatic Black males culturally navigate these types of social contexts. Using an exploratory qualitative design, three themes emerged including: (a) having a distinct cultural orientation, (b) hood socialization as a framework for persistence and resistance, and (c) negotiating support. The results from the study suggest that Charismatic Black males maintain connections to their community of origin and employ survival techniques to culturally navigate White two-year college spaces. The article concludes with a discussion and practical implications of these findings.