Since the United States' inception, the foundation of the country has been built upon inequities. From unfair assessment practices to ability tracking and arbitrary discipline, the African American/Latino K-12 educational experience has been exclusionary, subsequently paralleling the disproportionality for people of color incarcerated within the justice system. The disproportionality observed in special education programs and the prison system creates what some have called "second generation segregation" (Alexander, 2010; Ahram, Fergus, and Noguera, 2011; Ferri and Connor, 2005). While an emerging body of literature shows that persons of color who have disabilities and records of disciplinary infractions are more likely to be incarcerated (Peguero and Shekarkhar, 2011; Noguera, 2003; Ladson-Billings, 2004; and Ahram, Fergus and Noguera, 2011), this literature does not highlight the factors that set these students on the school-to-prison pipeline. Using Structural Inequity, Cultural/Social Reproduction, and Critical Race Theories, this qualitative case study examines the multiple factors in early home life and K-12 educational and discipline experiences of six formerly incarcerated individuals that may contribute to a pathway to prison. Findings suggest that for the study's six participants, historical and home trauma, environmental factors, and the quality of primary social relationships adversely impact K-12 educational functioning and precede the onset of criminal activities resulting in incarcerations for African American and Latino students. Drawing on these findings, I offer implications for schools, including the need for Trauma Informed Care pedagogy, early identification of special needs, Full Service Community schools that provide mental health support to students who have experienced trauma, and Restorative Justice practices including collaboration with local law enforcement. Implications for prisons include the critical need for education, employability skills, career readiness, and Restorative Justice practices. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]