This study takes an asset-based approach to understanding the academic experiences of African-American boys in their freshman year of high school in Chicago Public Schools. It uses both quantitative and qualitative methods to explore the overarching question: What factors are important for determining success for African American boys? By de-centering outcomes that we know (based on national and local indicators) will describe African American boys as the lowest performers, we can learn about where (i.e. adult interactions) and if (i.e. are their perceptions of schooling any different than their peers?) they need support. To do this, I quantitatively examine academic engagement among a cohort of freshmen in Chicago with an explicit lens to see if African American boys are perceiving classrooms in a way that would lead to them having lower engagement than their peers of other racial-gender subgroups. The findings of the quantitative work suggests that while students’ perceptions of classrooms are more important than their individual background or school-level characteristics, this relationship does not differ for African American boys as compared to other students. I also qualitatively explore the experiences of a subsample of African American freshmen boys to understand what drives notions of success for them. Adult relationships, especially with teachers, are an important factor in helping African American boys navigate their early high school experiences. Lastly, I conceptualize intentional teacher-student relationships that prioritize African American boys in a way that acknowledges societal views of this population and sustains them as learners.