This is a narrative qualitative study that utilized critical pedagogy as praxis and poetry as method to investigate how three African American males between the ages of 18 and 22 experienced juvenile delinquency in the Deep South and how their narratives engaged with the broader educational narratives on the school-to-prison pipeline. Through a non-traditional method, this study created a less exploitive space where the participants were free to narrate and co-analyze their stories without the sole interpretation of the researcher. The liberatory praxis space fostered through a workshop format provided a space for the once labeled juvenile delinquent and legally silenced voices of these young men to be raised to critical and emancipatory voices. Voices that questioned whether or not the circumstances(s) that contributed to their involvement with the juvenile justice system was attributed to an environment impregnated with racism that funnels the school-to-prison pipeline, and not just poor personal choice(s) often attributed to natural adolescent mischief. Through the collaboration of alternative and conventional research methods this study provided a closer perspective of the experiences of African American males who were encapsulated by the juvenile court system, knowledge necessary to understanding how through racial disparities, zero tolerance policies, and formal labeling the juvenile justice system funnels the school-to-prison pipeline. Their autobiographical poems are condensed but rich narratives of how they experienced juvenile delinquency and even now, as adult Black men, still continue to experience the impact of juvenile delinquency.