Disproportionately large numbers of Black youth experience repeated encounters with the juvenile justice system, and often these same youth present with a variety of school-related difficulties. Data from a sample of 842 Black males, assessed in five Ohio juvenile courts using the Global Risk Assessment Device (GRAD), are used to describe the different types of educational risks faced by these youth, including factors concerned with classroom behavior, student learning, and threats to academic progress. Additionally, the results of multivariate analyses are presented that provide support for the notion that disrupted family processes, delinquent peer associations, and mental health issues in combination present a compelling picture of factors associated with both in-class behavior and educational setbacks. At the same time, information is generated that points to the unique influence of mental health issues on learning difficulties faced by these court-involved youth. (Contains 2 tables and 2 footnotes.)