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In the US and UK, Black fatherhood has long been steeped in narratives of pathology. Despite the promotion of nuanced understandings of Black fatherhood in recent scholarship, research on Black fathers’ positive engagement with urban schools remains remarkably limited. Based on 20 in-depth interviews with a purposive sample of 10 Caribbean immigrant fathers in London and New York City, this paper utilizes critical race theory to highlight how some Black men attempt to counter racial subordination through masculine domination, particularly when engaging with white female teachers. The empirical analysis reveals that groups of Caribbean immigrant fathers draw on three common strategies to offset negative stereotypes about their engagement and assert their masculinities—namely distinctiveness, deference and dominance.