African-American male students are systematically forced to confine themselves to the social construct that European-American society has developed for them. Actions, behaviors, and words that communicate this message spread both interracially and intraracially within schools and affect African-American males tremendously in terms of their identity development and personal well-being. While many studies examine the overt forms of racism and more obvious microaggressions that African-American male students encounter in their schooling, few look at the deep-seated forms of racism that are less noticeable but that have a disastrous psychological impact on these students. This study shows the effects on the psyche and development of the three African-American male students involved as they retrospectively recount their secondary school experiences. Portraiture is used to capture each participant’s story accurately and clearly while critical race theory is interwoven throughout as theoretical framework for this research. Using both critical race theory and portraiture, a complete examination of how racism occurs within schools and its effects on African-American males is shown.