The purpose of this study was to explore the perspectives and strategies internal and external stakeholders used to support students in a career academy serving a predominately Latinx community. Within this case study, the principal of the school was Latinx, grew up within the same community as the school, and therefore shared the same culture as his students. Thus, we wondered how effective the principal would be in overcoming the cultural, political, and social barriers of students in the predominately Latinx school. We found the school leaders had a heightened awareness of organizational, cultural, and political complexities because of their own personal investment as well as their lived experiences of living and growing up in the community. The identities of the school leaders, then, led to a collective sense of agency and transformational leadership practices that facilitated a change in the grim situations and prospects of their students, and motivated them to become role models and community leaders providing resources and supports to ensure the high academic performance of students in the academy. However, we also realized that cultural understanding may sometimes lead to parochial views on what is best for students, leading to practices that prevent the exploration of student options beyond high school