Despite the expressed need for bicultural teachers, research on teacher attrition has demonstrated that a growing number of bicultural educators are leaving the classroom. Bicultural male teachers, in particular, experience high rates of teacher attrition. Schools, unfortunately, are contexts in which Latino male teachers are constantly experiencing dilemmas related specifically to both their gendered and racialized positionality as males of color. Grounded in Antonia Darder’s critical bicultural framework, this autoethnographic study explored the complex factors that drive Latino male teachers out of the classroom, through an in-depth and grounded examination of a Latino male teacher who left the classroom. The study contributes to the conversation on bicultural teacher attrition, gendered relations, and their relationship to both teacher preparation and the education of bicultural students. Furthermore, the study explored how racism, sexism, classism, trauma, and heteronormativity mitigate the experiences of Latino male teachers, and how these manifest themselves through the hidden curriculum, asymmetrical relations of power, gendered essentialism, policing of behavior, the culture of silence, conditions of isolation, and disabling cultural response patterns. The implications of such factors in the life of one Latino male teacher are carefully analyzed and discussed, in an effort to consider their significance in rethinking teacher preparation programs, with respect to the needs of Latino males. Moreover, the study offers an engagement with critical autoethnography as a significant tool of reflection in the educational process and emancipatory process of bicultural teachers.