Drawing on interviews that span over seven years, Derrick R. Brooms provides detailed accounts of a select group of Black young men's pathways from secondary school through college. As opposed to the same old stories about young Black men, Brooms offers new narratives that speak to Black boys' and young men's agency, aspirations, hopes, and possibilities. Even as they feel contested and constrained because they are Black and male, these young men anchor their educational desires within their families and communities. Critical to their journeys are the many challenges they face in public discourse and societal projections, in their home neighborhoods and schooling community, in educational environments, and in their health and well-being. In charting these challenges and the high stakes of the trials, lessons, and triumphs they experience, Brooms shows that we cannot understand the educational journeys of Black boys and young men without accounting for the full sociocultural contexts of their lives and how they make sense of those contexts.