Numerous studies and interventions have been designed to either reduce the prevalence of risky behaviors (substance use, sexual activity, etc.) or increase the level of educational activity for adolescents. Research suggests that these two constructs may be related yet little is known about this relationship among African American youth. Archival data from the Risk Reduction Project was used to explore the connection between the protective factors of educational aspirations/expectations and recent participation in risky behavior. Results suggest that recent use of marijuana, alcohol to the point of intoxication, and sexual activity predicted lower aspirations and expectations among African American youth. From a positive youth development perspective, this study suggests the development of holistic interventions that build educational assets in youth, in addition to working to minimize risk behaviors. Limitations and suggestions for future research are also discussed.