The anchoring weight of slavery continues to ground schools by design and implementation, 151 years after the 13th Amendment to the Constitution was ratified. Empirical literature is rife with evidence that Black and Brown youth are penalized more frequently and with greater harshness than their white, suburban counterparts for the same offenses (Gregory, Skiba, & Noguera, 2010; Welch & Payne, 2010), to the point where Triplett, Allen, and Lewis (2014) describe this phenomenon as a civil rights issue. The authors examine how a constellation of school-sanctioned discipline policies have connected the legacy of slavery with punishment. In order to curb burgeoning suspension rates that disproportionately target Black youth, schools and grassroots organizations have adopted various tiers of Restorative Justice (RJ). This article draws upon existing theoretical frameworks of Restorative Justice to discuss new approaches and directions, as well as the limitations of its hyper-individualized applications in K-12 schools. Finally, the authors assess two case studies that aim to transform schools and community engagement by refocusing restorative philosophy on the ecological conditions of student contexts, rather than the presumed intrapsychic symptoms habitually ascribed to youth behavior and Black culture.