Recently, the effects of school exclusion and criminalization of youth misbehavior has garnered much attention from the research community. The process associated with school exclusion and criminalization has been described popularly as a school to prison pipeline (STPP). Studies of school exclusion and criminalization repeatedly report evidence of disproportionate punishment, exclusion, and incarceration of Black and Latino students, as well as students receiving special education services. Although important, these studies fail to address the role of school leadership in mitigating or exacerbating negative outcomes for students within a STPP model. In this article, the author examines the literature on the characteristics of youth typically involved in the juvenile system. Additionally, he explores the ways that school leadership contributes to youths' exclusion and their involvement in the juvenile system. Finally, the author discusses ways that school leadership can intervene to mitigate exclusion and disrupt the cycle of negative feedback that results in the criminalization and incarceration of youth.