I pose a straightforward rhetorical question about disproportionality and endeavor to answer it with view to suggesting what can be done in terms of linking theory to practice. First, I frame disproportionality by asking where does it come from? Second, I describe multiple, interconnected historical phenomena to be considered when educators contemplate the complex topic of overrepresentation, ranging from the genesis of historical understandings of human difference becoming categorized into hierarchies of race, to the perceptions of race and dis/ability held by contemporary educators. Third, I argue that connections among these phenomena reified deficit-based understandings of vulnerable children and youth, creating a disabled population that, in turn, continues the status quo of disproportionality within schools. Fourth, invoking the concept of the personal is the professional, I discuss possible actions within an educator's control to help counter overrepresentation, while listing areas outside of school that simultaneously need to be focused upon.