This article reports on one teacher's year-long project seeking to disrupt the school-to-prison pipeline through class dialogue around gang affiliations. The review of literature defines the school-to-prison pipeline and its connections to gang affiliation. The study engaged methods of qualitative action research with seven male participants between the ages of 15 and 16 in a high school English classroom where they engaged in dialogue around gang affiliation and their experiences of criminalized schools. Findings provided some hope that teachers might play a role in disrupting the school-to-prison pipeline but that strong student-teacher relationships are necessary. Implications describe how other teachers wanting to disrupt the school-to-prison pipeline might use curricula that spark discussions around gangs.