Academic success for Black males has been a struggle historically in comparison to other student demographics. This study sought to understand the perceptions of students, teachers and educational leaders in regards to the achievement gap and the use of Culturally Relevant Teaching (CRT) strategies. This qualitative multiple case study addressed the problem that many educators and leaders of education do not possess the competency needed to effectively teach Black male adolescent students using culturally relevant practices in the areas of reading and math. Fourteen participants were included in this study. Through interviews, surveys, and naturalistic observations, I was able to explore how participants perceived and articulated their experiences with learning and teaching. Findings suggest (a) students perceived their academic difficulties to be a reflection of difficult work; (b) students perceived their academic difficulties to be a reflection of their classroom environment; (c) teachers have negative perceptions of Black male students and their learning experiences; and, (d) misconceptions and lack of knowledge prevent proper use of CRT strategies. In addition, this study provides further specification of the challenges of implementing effective CRT classroom practices and participants' lack of experiences with CRT trainings. Participants concluded that CRT strategies are imperative to their students' success, but they are not confident in their ability to implement them. The paper closes with a discussion concerning implications for practice and future research. [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.]