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Drawing on principles from Critical Race Theory, this paper explores Dominique Morisseau’s Pipeline as a politically urgent and emotionally resonant counterstorytelling that exposes the structural racism embedded within the American public education system. The play critiques the myth of educational neutrality and social mobility, revealing how schools often perpetuate the very inequities they purport to correct. Through the emotional and moral struggle of Nya—a public school teacher and mother of Omari, a Black teenager facing expulsion —Pipeline dramatizes the profound discrepancy between institutional ideals and lived realities. Morisseau presents the classroom not as a space of equal opportunity and freedom, but as a site shaped by racial bias and race-based assumptions. Omari’s anger is not depicted as a mere behavioral lapse, but as an expression of generational trauma, and the systemic pathologization of Black male youth. Furthermore, Morisseau integrates intertextual references to Gwendolyn Brooks and Richard Wright, using them to explore Black anger as a historically rooted and collectively inherited response to systemic oppression. Ultimately, Pipeline invites critical reflection on the school-to-prison pipeline, urging its recognition as a systemic and urgent form of racialized educational injustice.