This qualitative study sought to advance understanding of the specific behaviors, actions, and skills utilized by a principal to create a college-going culture that ensured underrepresented students college access and success. The study was bounded by an exemplary urban high school serving underrepresented students in the northeast region of the United States. The researcher investigated various conditions at the school through a single, instrumental case study. Individual interviews with the principal (the primary research participant) and 10 secondary participants (three teachers, three counselors, four students), on-site observations, and analysis of various relevant artifacts, documents, and extant data sources comprised the main sources of data in this study. The researcher utilized a systematic, iterative, and reflective process to organize, code, and categorize the data. A constant comparative method was then applied to determine emerging themes, and subthemes, represented in thick, rich descriptions. Findings illustrated how the principal of an exemplary urban high school served as a symbolic and cultural leader, implemented resources and structures that ensured access to a rigorous, college-preparatory curriculum for all students, promoted caring relationships and a supportive environment, developed students’ sense of resilience, challenged educators’ mindsets, and established high expectations for teacher and student performance. Findings revealed a set of leadership values, actions, and skills utilized by the principal as means to embed relevant structures, relationships, and a growth mindset within the school’s culture. These findings have the capacity to provide urban high school principals the necessary tools to implement effective college-going cultures within their school communities.