The underperformance of African American males compared to their white counterparts in educational settings has been a long-standing research subject. Researchers have employed several lenses with which to view this phenomenon. Ogbu (2004) claimed that African American students are more likely to possess anti-school attitudes, which ultimately lead to disconnection from school. These anti-school attitudes serve as a mechanism to disengage from an institution that is viewed as an instrument with which to perpetuate white supremacy. Steele (1992) asserted that Black students' contact with society's stereotypes of their ability is often internalized as "inferiority anxiety." This anxiety can result in blaming others for their underachievement, avoiding available opportunities, and developing a victim's mentality. This qualitative inquiry aimed to understand the lived experiences of African American adolescent males as they steer through societal constructs, racism, and stereotypes. This study examined the impact of eight Black teenage males' racial identity on their education and how this identity impacts school connectedness. Findings suggest that African American students felt a strong desire in their environments to dispel some of society's negative perceptions about them, specifically their connection to the school. Respondents in the survey attribute this to the guidance they felt from a strong adult influence in their lives, whether from their family or a teacher at school. Decision-makers in the world of education should consider avenues of support for African American male students who carry a proverbial heavy load when they enter the school's front doors. The messages that they see and hear are impossible for them to ignore. However, their insight holds hope that schools can actively foster a connection for African American male students to school. The findings also suggest that school leaders should carefully examine curriculum and professional development to ensure that culturally responsive practices support the success of all students. Additional considerations for school leaders include innovative hiring practices to provide African American male students with greater access to staff members with a shared life experience. [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.]