In this article, I explore how the social contract of schooling and the three functions of schooling (Noguera 2003)—to sort, to socialize, and to control— impact and constrain the freedom and agency of a group of young Black and Latinx men in one suburban school district that was experiencing sociodemographic shifts in the Northeastern United States. I use qualitative data to frame how the young men experience schooling, and I show how the local community context facilitates the institutionalization of discriminatory sorting processes and racially prejudiced norms. I also show how the young men are excessively controlled and monitored via zero tolerance disciplinary practices, which effectively constrains their humanity and capacity to freely exist in their school and which inadvertently strengthens the connective tissue between schools and prisons.