Black students attending US K12 school districts have predictable results (Darling-Hammond, 2007). These schools demonstrate disproportionate results in all indicators of school success. Leaders of these schools are expected to improve student outcomes that disrupt and dismantle systems that have historically perpetuated these results by leading and developing change initiatives that directly improve conditions for Black children. However, many leaders do not have the preparation, skills, or support to complete this task. This is a case study of John Hope Unified Schools, pseudonym, a medium-sized district in the Bay Area. The research was examined through the lens of SystemCrit, a developed conceptual framework that blends General Systems Theory and Critical Race Theory to investigate the relationship between central office and site leaders. The study used four data sources to identify four themes: commitment to student outcomes, the impact of racial dynamics, the importance of accountability, and challenges faced by site leaders in transforming their practice. The study found that the case district has a communicated expectation of all leaders to work to improve conditions for Black students, deep commitment to racial equity learning and leadership, internal mandates lead the work, and external mandates can be leveraged to create conditions for change. Mandates are authoritative commands or authorizations given by a governing body or organization. Internal mandates, such as board policy, administrative requisitions, and cabinet-level procedures, come from within the system. External mandates are imposed on the system by outside governing bodies, such as county, state, or federal requirements. Additionally, the research showed that the participants identified several challenges to change, including, but not limited to, resistance or fear of change, racial resistance, resistant or reluctant staff, and staff distrust of district initiatives. Participants also noted central office bureaucracy as a barrier to transformative change. The study highlights the complexity of the site leader role as both challenging and extensive. The recommendations assert that district office leadership must intentionally prepare site leaders to undertake significant transformative leadership work. School district leaders are responsible for supporting these leaders in leading for change. As a system, these individuals must nurture and develop these leaders. Central office leadership should provide site leaders with the necessary resources, support, and encouragement to do the hard work, including assisting them in addressing historical racial inequities that continue to hinder Black student success. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]