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In this paper, I draw on pedagogies of acompanamiento (Sepúlveda, 2018) to explore how educators in a largely Latinx and African American high school attempt to build relationships with parents and develop a sense of belonging in their school. In this 3-year critical ethnographic study, I analyze how the principal leverages his immigrant identity as a “border broker” in helping families find a sense of belonging in the school and community. However, I also explore how in a community fragmented by racialized divisions, these pedagogies of acompañamiento may be perceived as exacerbating divisions. I argue that a wider view of border-crossing experiences—and shared struggles—can be a vehicle for developing belonging and solidarity in a divided Black and Brown community.