DescriptionOne of the prominent questions educational research has focused on has been, and continues to be, inequities in education as it pertains to the disparities in academic performance among different groups of students. Specific attention has been paid to male students of color and addressing the disparity in high school graduation rates because it can have long term economic and personal consequences that range from joblessness to incarceration. This paper explores the experiences of young men of color in the Bronx, NY, and the academic outcomes of participation in the Umoja leadership program. The Umoja program is an all-male Brotherhood that focuses on leadership development and communication throughout the summer and during the school year for 22 students in grades nine through twelve. Findings from this mixed methods case study document the many tensions and conflicting expectations students face as members of their community such as being targeted members within their community who are expected to “fail” while also being expected to carry the torch and meet high expectations. Other findings suggest that the program’s focus on leadership helps refine the leadership and communication skills many young Brothers already possessed. Additional quantitative findings show that Brothers in the program saw an average increase in grade point average (GPA) and credit accumulation (CA) every year that they were involved in the program, and highlights that the program has a 98% graduation rate. Through these findings the researcher makes recommendations for program revisions and further study.