We center the voice of Dwyan Moore, a Black 12-year-old boy, during his transition of being diagnosed with a learning dis/Ability. We do so to grapple with the problem of disproportionate representation in special education along race and dis/Ability, with particular attention to educational leadership. Disproportionate representation is a reminder of the legacies of slavery and eugenics in United States public schools. We must address this enduring inequity. How we think, feel, and discuss such issues has systemic educational and equity implications for Black, Indigenous, and Youth of Color with dis/Abilities such as Dwyan. We end by promoting critical reflection and activities among educational school leaders on how student voices and agency can be included in dis/Ability transition planning and programming.