A qualitative exploratory study was completed to examine factors and processes associated with high school graduation among Black males in high risk urban contexts. Participants included 11 Black males between the ages of 19 and 35, who have graduated from high schools in some of New Jersey's poorest and dejected urban districts. These Black men were interviewed to determine what protective factors and processes contributed to their school persistence. Additionally, the study sought to examine commonalities among these men that led to high school graduation. Analysis of these interviews was completed using the grounded theory approach (Strauss & Corbin, 1997) and case study method (Yin, 2009). Results indicate that there are a number of important factors and processes that contributed to the participants' ability to complete high school in environments where up to 65% of Black males fail to graduate. Broad themes associated with school persistence among these men included individual, family, peer, community and teacher factors. More specifically, the results revealed that the role of mothers in the lives of these young men was substantial. In fact, the majority of participants credit their mothers for their success. This is counter to much of the research that discredits single parent mothers. As well, these young men did not come from highly educated families, but there was a tremendous emphasis on education within their homes. Consistent with other work in this area, participants indicated that access to, and utilization of, community resources was vital to their success. The importance of the school environment, as well as the importance of support and availability of school staff and teachers was emphasized repeatedly. Other specific themes and commonalities are presented. Implications of these findings are discussed and recommendations are made to young Black men, parents, teachers and other school professionals.