In this article, the authors explore the sources of gender variations in African American middle school students' academic performance. The roots of Black males' underachievement are of particular interest. Because middle schools are essential links in the sequence of opportunities to learn, it is imperative to understand the social and educational forces that influence academic outcomes for this age group of adolescents. The authors examine the contributions of family, school, and individual factors to academic outcomes. Using survey research data gathered from a representative sample of middle school English classes in the Charlotte-Mecklenburg School (CMS) system, the article investigates how the various factors contribute to academic outcomes as measured by students' North Carolina End-of-Grade (EOG) standardized test scores. Findings indicate that although there are no gender differences in achievement in 2nd grade, differences become evident by middle school, with females obtaining higher test scores and grades than males. Although prior achievement and track placement affect all students in expected ways, males' test scores are more likely to be affected by peers, educational attitudes, school structure, and school climate. Females' test scores are more likely to be influenced by family socioeconomic status and cultural capital. The article shows how 8th-grade Black males' lower level of academic performance begins to take shape and to align in ways that foreshadow the disappointing school outcomes associated with older Black male students. (Contains 4 tables.)