The marginalization of young men of African descent has been documented throughout the African Diaspora. Black males in Bermuda are less likely than their same age peers to graduate high school or gain advanced degrees. They earn less than White Bermudian men and are almost twice as likely to be unemployed. This study explores the risks that lead a disproportionate number of Bermudian Black males to become disconnected from formal employment and schooling, and offers some insight into the gender gap in educational attainment. This study utilizes qualitative data from semi-structured interviews with Black Bermudian men, ages 18-30, who were out-of-school and unemployed (n=22; mean age=22.3) and with Black Bermudian boys and girls in their first year of high school (n=35; mean age=14.3). Findings reveal that Black Bermudian youth are experiencing high levels of exposure to family stress and community violence. The men in this study also recalled school relationships that emphasized disciplinary sanctions that left them feeling stigmatized, and the majority report that they were ‘kicked out’ of high school. Fears of repeated failure inhibit re-connection to formal institutions of work and school. High school first years report the beliefs that boys are more likely to get into trouble and are less educationally focused than girls, and girls are more likely to seek out, and obtain, social emotional support. This study contributes to our cross cultural understanding of the important role that families and schools play in the educational attainment, and consequent earnings, of Black males.