Survey and focus group sampling of students in high achieving schools compared to lower achieving schools were used to examine why there are fewer black men graduating from high schools in New York City as well as high schools around the country compared to other groups of students. Race is disaggregated in order to look at the difference in achievement rates for African American, black Hispanic, African, and Afro-Caribbean men. The findings support the contention that foreign-born blacks do better academically than native blacks. Students report violent schools, teachers who do not make learning relevant, and apathetic teachers and staff hinder learning. The findings intend to inform the development of programs, designed to address the needs of black male students who attend John Jay, other City University of New York colleges, and schools across the country. Given the interest in growing incarceration rates and penal policy, this research explores proactive measures for dealing with at risk youth, e.g. creating tutoring and mentoring programs, recruiting and retaining more teachers and administrators who represent the student body, and diverting first time offenders.