This study uses two waves of data to examine the relationships among racial socialization, racial discrimination, and academic achievement outcomes in a sample of 144 African American male adolescents. Using latent class analyses, the authors identified four patterns of adolescent-reported racial socialization experiences: Positive Socialization, Moderate Negative, Self-Worth, and Low Frequency. Discrimination experiences were associated with subsequent academic performance. Wave 1 racial socialization experiences were associated with academic persistence and performance at Wave 2. These findings suggest that various patterns of racial socialization practices have the potential to improve educational outcomes for African American boys, particularly in the context of their experiences with racial discrimination. (Contains 3 tables and 1 figure.)