Purpose: Despite the difficulties students encounter during the freshman transition, the phenomenon remains an understudied topic in education. The purpose of this collective case study was to gain an understanding of the Grade 8 to Grade 9 transition experience for African American male students in one suburban school district. Furthermore, this research sought to determine what programs and procedures could be put in place to aide African American males in their transition to high school. It is important to understand how African American males are impacted by the freshman transition because the statistical data indicates that they are the group most likely to drop out of school and are doing so at disturbing rates. Additionally, African American males are the sub population most adversely impacted by the economic conditions associated with not having a high school diploma. As such, Critical Race Theory served as the conceptual framework of this study. Method: Four African American male administrators participated in this collective case study and data were collected using face-to-face interviews conducted in person and via Zoom. In an effort to add African American male administrators' voices to the literature, In Vivo coding was utilized. Therefore, an important stakeholder group has been added to the freshman transition literature. To triangulate the data gathered from the participants, data were also gathered from school counselors. The counselors who completed an online questionnaire were employed at schools where a participant/administrator worked. Findings: The participants identified "positive adult relationships" and "connectedness" as vital to their own successes during the freshman transition. In regard to programs and procedures that would benefit contemporary African American male students during the freshman transition, three themes emerged from the data. The participants believed that establishing a "mentor" program would benefit African American male students during the freshman transition. They also believed that "training" and "connectedness" were important factors for the success of African American male students. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]