This case study examines how relationships with staff in a GEAR-UP (Gaining Early Awareness and Readiness for Undergraduate Programs) pre-college program positively influenced the college-going aspirations of Black ninth-grade students. Critical Race Theory and Possible Selves provide an intersecting analytical framework for understanding the formation of students' college-going aspirations. Findings speak to how the role of student leaders in the program assisted high school students in forming college-going counternarratives and provided possible buffers to stereotype threats about what is academically possible for Black youth. In addition, findings demonstrate how the GEAR-UP program served as what I have conceptualized as an educational "Community of Possibility."