Although school districts in Florida have reported a decrease in the overall dropout rate, the dropout rate among African American males remains higher than it does for any other ethnic group. Guided by Ogbu's oppositional culture theory, the purpose of this phenomenological study was to investigate the high dropout rate among African American males and determine some of the social, cultural, educational, and economic elements that may hinder African American males from completing high school. A purposive sample of 10 African American males who dropped out of high school and who were between the ages of 18 and 35 was selected to participate in this study. Thirty open-ended interviews were conducted, and the data were analyzed using an open coding system. Twelve themes emerged that provided evidence of the complex factors associated with dropping out. The major themes included lack of motivation from parents and teachers, disengagement from the educational institution, economic challenges related to poverty, and peer influence. It is recommended that programs and curricula be developed and implemented that would create opportunities to build positive relationships between African American male students and their teachers, parents, and peers. Positive social change could occur with an increase in the graduation rate of African American male students, which would offer a more educated work force for the community.