Bronfenbrenner’s ecological systems theory highlights the influence multiple systems can have on one’s development. Taking into account multiple systems that can influence one’s identity, the introduction of ethnic-racial socialization (ERS) as a practice to further influences one’s identity at multiple systemic levels was introduced to create framework of Black males’ academic identity development. This study utilized aspects of Bronfenbrenner’s ecological system theory and ERS practice to test different variables related to the formulation of Black males’ academic identity, educational expectancy and academic achievement. The purpose of this study was to develop and test a model that incorporates family, school, and communal factors in predicting Black males’ educational expectancy and academic achievement. Multiple system levels, including family, school and communal support were tested at different time points as related to educational expectancy and academic achievement. The nationally representative sample, High School Longitudinal Study: 2009, was used for this study. The research utilized this national representative study to analyze a sample of Black students’ (N = 1,280) support, parental expectations regarding students’ educational success, students’ education expectancy, and academic achievement. The use of only Black participants was purposeful in this study, due to the underrepresentation of Black students in indicators of high academic achievement and the overrepresentation of Black students in indicators related to low academic achievement. Because estimates suggest 40% of Black males drop out of high school, the study tested hypotheses related to support and academic achievement, support and educational expectancy, and educational expectancy and academic achievement. To test the hypotheses, confirmatory factor analysis, structural equation modeling, and hierarchical linear regression were utilized to test regression paths, mediation, and moderation models related to the variables of interest. Results showed mixed support for the study hypotheses. While preliminary measurement model modification indices led to dismantling the family support variable and eliminating indicators from school and communal support, the final measurement model demonstrated good model fit. After testing the measurement model, a full structural model with the observed variables related to support, educational expectancy, and academic achievement were tested. The results from the full SEM model indicated a significant relationship between educational expectancy and academic achievement. The final model implored bootstrapping to test the direct, indirect, and total effects of the full SEM model with control variables. The results indicated that communal support had a significant relationship with academic achievement through parents’ educational expectations for students. Additionally results indicated that family financial support had a significant relationship with academic achievement through parents’ educational expectations for students. Moderation analysis was used to test if parents expectations for students moderated students educational expectancy and total grade point average (GPA). The results did not significantly support moderation. Overall, findings support a systemic, multi-level influence of support on Black males’ academic identity development and later academic achievement. Strengths of the study, limitations, and implications for future research and school professional and mental health clinicians were presented.