For years researchers have stressed the importance of implementing a Culturally Responsive System to improve outcomes for Black students (Culturally Responsive Sustaining Education, 2018). It is important to shift towards a perspective that sees everyone from an asset-based perspective The narrative that was created throughout time was that Black students' lack of success in school was the result of a lack of intelligence, lack of motivation, and /or family dysfunction (Hammond, 2015). Howard (2013) opined that the focus on Black students from the perspective of being poor and living in challenging environments takes away from the fact that educators are not prepared to work with Black students. The purpose of this qualitative, comparative case study was to explore the system leader's understanding of the organization's level of cultural competence and the fidelity of implementing culturally responsive sustaining practices that lead to the improvement in outcomes for Black students. There were three school districts with at least 20% percent Black students and a Black graduation rate of at least 80% in two BOCES regions in New York State that participated in the study. The graduation rate for the Black students in each district was 80% or higher for the 2019 school year. The study consisted of a comparative analysis to answer four research questions. Data were collected through open-ended interview questions of 11 leaders across three districts and a review of relevant documents. Data for each research question were first analyzed by district and then compared across districts to synthesize similarities, differences, and patterns in system leaders' understanding of their organization's level of cultural competence that led to improved outcomes for black students. The study resulted in 16 comparative findings. There were 12 conclusions that emerged from the findings. Four key conclusions are that culturally responsive school districts understand the needs of the learning community; develop relationships with students and build partnerships with families and universities; hire for diversity; and allocate fiscal resources for programs, staffing and learning spaces to assist students in transitioning from dependent to independent learners. This study will help educators understand the role system leaders play in creating culturally competent districts that increase not only opportunities but also student achievement for Black students. [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.]