This qualitative study encompasses the voices of five Black middle-class male participants in college on their kindergarten through high school journeys. The field of research often studies Black boys from lower socio-economic status with a deficit lens when examining the achievement gap. Bhattacharya (2017) phenomenology research was utilized to examine the lived experiences of middle-class Black male college students and how race, class, and gender inequalities shaped their educational experiences. Multiple themes consistent with the literature regarding barriers for middle-class Black males were present in the data; however, multiple new themes emerged including racial socialization, internalized oppression and Black middle-class educational culture. The results of this study highlighted the impact of trauma by racist microaggressions within the educational structure on young Black males, the power of teacher perception, and Black middle-class educational culture. This qualitative study offers implications for the field of education and policymakers by increasing awareness of how the culture of Black middle-class families and the educational system impacts Black boys. Additionally, there is professional development the education field could benefit from that will promote authentic Black male student agency across all grade levels. Recommendations for future research include deeper examination of parenting structures and the impact of teacher perception on Black middle-class males. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]