Leadership is a critical component of creating and sustaining a school culture that promotes the inclusion and success of students. The purpose of this study was to examine how school leaders helped to enact and sustain a reformed Advanced Placement (AP) culture designed to increase participation and success of students of color. Building on existing work of transformative leadership, this study describes the experience and challenges of educational leaders in understanding how leadership practices change the AP culture. The case study method examined one mid-sized urban district in Southern California that utilized transformative leadership. The methods included 15 open-ended interviews with educational leaders in a variety of capacities (i.e., district leadership, school administrators, counselors, and teacher leaders). The findings demonstrated critical components leading to deep and meaningful cultural change in AP. The analysis showed leaders in this district, who sought equity, were driven to create meaningful change, and were grounded in the community. Being grounded in the community had a great impact in promoting a transformed culture at the classroom, site, and district level.