This qualitative study explores some of the most persistent and significant racial gaps in our society today, focusing on the intersections of race, academic achievement, and criminal incarceration via an analysis of the K- 12 experiences of African American criminal offenders. The purpose of this research is to gain additional knowledge and insight about the racial disparities that persist in academic achievement and punitive methods of social control, hopefully contributing to the ongoing discussion of the ways in which to improve teacher practices and develop strategies for effectively engaging African American males in the classroom. There were three participants in this study, all adult African American males with varying levels of school success who have been criminally incarcerated. Each participant was interviewed about his school experiences. The interview data was analyzed and coded, and three primary themes emerged: school engagement, race, and violence. While incidents involving race and violence were present in each of the participants\u27 stories, the participants\u27 level of school engagement seemed to have the most profound effect on academic achievement and subsequent criminal involvement