Hispanic males represent the highest high school drop-out rate of all minorities. Given the 82% projected increase in the Hispanic school-age population in the next 25 years, an understanding of the factors that assist male students to overcome common obstacles in order to succeed and complete high school is vital. This dissertation study examined the factors that appear to have helped six Hispanic male students to overcome obstacles in order to achieve academic success. Using a case study approach, I collected information through in-depth interviews with students and each of their mentors, and conducted a thorough review of each student's school records. The results indicate three primary factors that assisted students in achieving academic success. They are: (1) the role of family, specifically parents, siblings and the mother; (2) self-knowledge, as it relates to self-awareness, self-understanding, internal locus of control, responsibility and internal motivation and drive; and (3) the importance of adequate and reliable adult support. Subcategories of these findings, their implications and suggestions for future study are explored and discussed.