This study focused on various ways retired school principals conceived leadership identity and accounted for involvement in special education with students identified or identifying as disabled. Participants’ narratives regarding what it meant to be involved with special education and/or disability and relationships between conceptions of involvement and identities served as primary data. Conceptions included, but were not limited to, perceived ways participants viewed their attentiveness and commitment to special education. In this study, identity was understood as a professional identity in relationship to one’s social identities and in response to others’ social identities. Employing a phenomenographic approach, findings were grouped into pools of meanings, labeled as categories of description, and presented in an outcome space. Findings evinced participants accounted for involvement with special education and/or disability through professional responses, risk-taking, and working toward socially transforming their schools. They experienced involvement as active presence, critical reflection, advocacy, and resistance. Findings suggested participants’ involvement in special education was influenced by personal experiences with disability and relationships with individuals with disabilities. Participants experienced identity through compassion, learning, spirituality, and dis/abled-ness. Discussion of how leadership preparation programs can recruit and prepare school leaders in special education is provided.