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Calls for men of color to become K-12 teachers have received special attention in education policy. In California, this effort became “first on the agenda” (Fensterwald, 2019). This qualitative study employs the lenses of Critical Social Theory and Critical Discourse Studies to analyze the experiences of high-performing Latino boys and their Latino male teacher. Findings presented challenge linear thinking that merely adding Latino men in the classroom will automatically improve academic outcomes. Findings presented highlight the delicate, complex nature of student-teacher relationships between Latino men and Latino boys. This research aims to illustrate the underlying processes that both inhibit and propel positive relationships, as well as ways to foster a transformative learning experience for Latino boys.