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School districts across the country share the challenge of recruiting and retaining Black male teachers. However, most literature explores this phenomenon theoretically with little input from the targeted demographic. Utilizing a critical race theory lens, this phenomenological study explored the perspectives of Black male teachers on how and why Black male teachers struggle to enter and remain in the field. Findings indicated that Black male teachers' voiced concerns about isolation, backlash to pedagogical expression, misalignment and issues in teacher education programs, and economic instability as factors that impact their ability to enter and remain in the teaching field. This study points to the need for culturally responsive and community-focused reforms to teacher education and development processes.