© 2017 University of Massachusetts Amherst College of Education. This research examines academic experiences of African American males (ages 18–25) who attended urban schools in southern California. The participants were incarcerated for at least one year prior to being housed in a pre-release program where they reflected on their academic experiences and perceptions of the school environment. The participants' academic experiences reflect many of the stories of young African American males in public schools. Data were collected from individual and group interviews, questionnaires, observations, and short writing responses providing a unique perspective within a critical race theory framework. Participants' early academic experiences were most positive during kindergarten and declined as they grew older. The academic experiences of these young men seemed to profoundly impact their social, cultural, and psychological development as well as their life choices, which may have led to incarceration.