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In this article, I explore how narratives surrounding Black male academic achievement, while once focused on professional sports as a “way up, way out,” have been exchanged for a hip-hop focused, “hustle” pedagogy. Using a qualitative case example of 12 young Black homeless males and a possible selves framework, I argue that hip-hop based education (HHBE), in the hands of informal educational staff and the white gaze, limits the possible selves of Black boys in pejorative, socially reproductive ways. I conclude with the implication that, in our efforts to quickly solve the educational crisis facing young Black men, we continue to fall short of creating equity-focused policies that places the future success of young Black males at the center.