Based on a case study of two majority-Black public high schools in a highly segregated American school district, the article employs a critical intersectional framework to examine the experiences of ten college-aspiring young Black men as they navigate the college choice process. Findings indicate that working-class Black male students are less likely to have access to college-going resources and social networks than their middle-class peers. However, a well-resourced school that affirms Black identity may increase agency and help crystallize college plans among working-class Black male students. In contrast, the study found that more institutional academic structures constrain agency and channel working-class Black male students towards under-resourced colleges where they are less likely to thrive.