The representation of African American male teachers in elementary urban schools has decreased. The purpose of this basic qualitative study was to investigate administrators' and African American male teachers' perceptions of how administrators are challenged to support the retention of African American male teachers in elementary and middle schools in the focus urban school district. Social, cognitive, and transformational leadership theories were used as a framework to guide the study. Research questions addressed how administrators perceive the ways they support the retention of African American male teachers and how African American male teachers perceive that support. Purposeful sampling was used to recruit eleven African American male teachers and eight administrators to participate in this study. Data were collected using semi structured interviews and thematic analysis. The interview responses were transcribed and examined through thematic analysis, which identified codes and themes derived from the transcripts. The three key findings that emerged from the data were (a) climate and culture, (b) developing strong relationships and collaboration, and (c) support and professional development. The findings identified leadership practices that supported challenges influenced by student achievement, professional growth, and African American teacher retention. Further recommendations include the findings from this study may contribute to a positive social change of African American male teachers' presence in school settings and improve effective leadership supports provided for African American male teachers in urban schools. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]