The purpose of this theoretical study was to explore, examine, and analyze the United States (US) Zero Tolerance (ZT) educational policies and practices of the school-to-prison pipeline phenomenon. This study specifically explored the influence of the ZT policy on African American males becoming part of that system. The study was guided by three research questions: 1) how do the U.S. educational policies and practices of ZT methods and the current application influence the expansion of African American males into the school-to-prison pipeline; 2) who benefits from these policies and practices of ZT and the school-to-prison pipeline; and 3) how do these educational and criminal justice policies entrap African American males? This study further examined the impact of race, regarding the disproportionate numbers of African Americans males that are trapped within that system. In addition, this study's research methodology adopted a critical theory and a critical race theory application, utilizing two case studies of African American males involved in the school-to-prison pipeline, to get a better understanding of existing trends. Research suggests that ZT educational policies and the school-to-prison pipeline phenomenon have profound consequences for African American males being funneled into that system. The findings are also consistent with current research literature indicating that ZT and the school-to-prison pipeline, serves as a gateway for future criminalization and incarceration of African American male students into the prison industrial complex.