Common discourse concerning the educational trajectories of African American males consists of dismal future outcomes due to defective schooling experiences in kindergarten through twelfth grades. There has been a disregard of counter narratives of high academic achievement and overall school success coupled with a highlighting of failure through deficit-based research practices. Consequently, African American males are positioned as delayed or troubled, which serves to perpetuate educational inequity. This study attempts to increase the scarcity of literature by giving voice to the experiences of high achievement among African American adolescent males attending a school designed to support the achievement of impoverished youth of color. Interpretative phenomenological analysis was used to investigate the lifeworlds of nine African American males in seventh and eighth grade at a private, college preparatory middle school in southwestern Florida. Individual, semi-structured interviews were conducted regarding their experiences of academic success. The results indicate that these young men developed positive scholar identities through a process that included the cultivation of academic achievement, sacrificing to succeed, trailblazing, striving for the good life, and planning for success while simultaneously rejecting deficit-based and peril portrayals of Black males. Practical implications for school psychologists, educators, and parents are discussed.