Combining poetic inquiry (Davis, Qual Inq 27(1):1–11, 2019) and the group conversation method (King and Mitchell, Black mothers to sons: juxtaposing African American literature with social practice. Peter Lang, New York, 1995), this chapter investigates the educational leadership of Maryland’s Principal of the Year and the principal of Baltimore’s Dunbar High School, Dr. Yetunde Z. Reeves. This collaborative investigation illuminates and harmonizes the voices of this accomplished principal and three other Black women educators/coinvestigators. The coinvestigators include an African-centered education researcher, an artist and arts-based qualitative education researcher, and a professional development consultant who is partnering with the principal and her staff to cultivate a transformative “culture of care” building relationships and fostering positive classroom and schoolwide environments with students, families, and each other. This reflexive critical inquiry asks: How does the principal’s leadership embody creativity? Does her leadership entail dimensions of African American culture/Africanity (Boykin, The academic performance of Afro-American children. In: Achievement and achievement motives. W.H. Freeman, San Francisco, 1983)? To what extent do creativity and Africanity equip her to do revolutionary/transformative educational leadership? Significantly, we will amplify what creativity in the principal’s transformative culturally relevant leadership praxis means distinct from what is understood as creative educational leadership. Also, the process of critical poetic inquiry, distinct from poetic inquiry and literary poetry, uses poetic devices to critically analyze the research inquiry to advance movement toward relevant forms of justice while producing research poetry as a collaborative product. We analyzed group conversation transcripts to identify key themes and co-construct research poems to reflect these themes and respond to the research questions. Using these methods of inquiry and analysis, we acknowledge that our critical focus on the role of culture in urban school leadership enabled us to reflexively include our lived reality as African women, education researchers, and practitioners whose positionalities beyond normative conceptions of “race” and “gender” were both transposed and informed by the data during the analysis process: We see this as an added significance, benefit, and contribution to the literature.