Drawing from the lenses of critical race theory (CRT) and Pierre Bourdieu’s notion of habitus, this article compares the Jackie Robinson story with the Brown versus Board of Education narrative. This juxtaposition illustrates the similarities of these narratives and how interests converged racially. By comparing these historical narratives, we show that there are significant racial contingencies African Americans must internalize to integrate into society. In this sense, we argue that the Jackie Robinson story serves as a powerful and problematic pedagogy for Black males to be part of mainstream society—what we call "expected racial habitus."