After one of my students correctly answered a question that everyone else was struggling with, I eagerly approached him to give him a high five or fist bump, which was apparently not hip enough for him. Instead, he suggested we do a different kind of handshake involving a lot of different twists, finger combinations, and intricate patterns. By being included in this handshake, I felt like after two short weeks my students were beginning to accept me and were welcoming me into their personal lives. Little did I know that I had just participated in a gang affiliated handshake; the class erupted in laughter and I was told I was gangbangin' and officially a part of the clique, aware of their secret knowledge (Researcher Journal, 2 October).In this situation, what should a teacher do? Clearly the students found this moment funny and interactive, an invitation into their lives through a display of extra-curricular language and action. However, a teacher might be concerned that handshakes and signs representing gang affiliation might be used by others to criminalize students within a school setting (Butler et al., 2012; Gregory, Skiba, & Noguera, 2010; Noguera, 2003; Skiba, Rausch, & Ritter, 2004). The question, What should a teacher do?, when gang issues and identities enter the classroom only scratches the surface: Are my students involved in gangs? How might that involvement (real or perceived) affect their education? How might that involvement (real or perceived) affect the way disciplinary policies push them into the school-to-prison pipeline? How might I disrupt the school-to-prison pipeline? Can I make any difference?Over the course of a year, the researcher wrestled with these questions, engaging action research to explore how to disrupt the school-to-prison pipeline through a curriculum purposively designed to generate dialogue around gangs and gang affiliations. This report of research opens with a review of literature defining the school-to-prison pipeline and its connections to gang affiliation. The study engaged methods of qualitative action research to record and analyze the researcher's experiences as a high school English teacher in dialogue around gang affiliation with adolescent male students experiencing 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 schoolto-prison pipeline might use curricula that spark discussions around gangs.DEFINING GANGThere is no internationally accepted definition of the word gang (Howell & Griffiths, 2016), but even in this article it has already been used it as if a reader will intuit its meaning. Current federal law defines a criminal street gang as anongoing group, club, organization, or association of five or more persons that has as one of its primary purposes the commission of... a federal felony involving a controlled substance...; a federal felony crime of violence that has as an element the use or attempted use of physical force against the person of another; and a conspiracy to commit an offense. (18 USC § 521 [a, c])While researchers are not always specific about drug crime or violence in using the word gang, the historical development of gangs from the 1980s to the present must recognize the effect of the international drug trade on local gangs (Toldson, 2012). Other labels used in the research include adolescent gangs (Mallett, 2015), street gangs (Toldson, 2012), and delinquent peer groups (Barnert et al., 2015). In this article, the word gang connotes all of these possibilities because the participants in this study used the word gang to describe such groups. When referring to students with gang affiliations, the students claimed those affiliations; there were no assumptions that the participants were involved in delinquent or criminal activity. …