The prison-industrial complex penetrates the public sphere through enhanced and militarized police presence in poor neighborhoods, thereby playing a key role in mass incarceration, and intersects with public schools via zero-tolerance policies that push students out. The purpose of this article is to examine how the Juvenile Justice System (JJS) impacts the educational experiences of Black males. Specifically, we present a case study of Malcolm, a multiracial (Black, Latino, and Native American) male who had been part of the JJS for the last five years. We articulate Malcolm's schooling and JJS experiences to discuss how the prison industrial complex and school-to-prison pipeline intersect to push marginalized youth of color out of schools. We conclude by listing a set of recommendations in which Malcolm provides key strategies to reform the JJS and school-to-prison pipeline.