Despite a long-standing history of structural and institutional challenges, there are a significant number of Black males who achieve positive academic outcomes. This article examines Black males who attended college after graduating from an all-male, predominantly Black Charter High School in the Mid-Atlantic region of the United States. Findings suggested three types of trust helped participants achieve college attendance; trust in themselves, trust in close others, and institutional trust. Examples of differing types of trust are highlighted, as well as implications for building trust in schools in the future. The findings from this article demonstrate that trust can be established when institutions are willing to provide a safe, nurturing environment which recognizes the inherent strengths of all students.