Purpose: For culturally responsive practices (CRPs) in schools to be successful, educational leaders must look outside of the school and consider school, district, and system-level policies and practices that influence the sustainability of culturally responsive classrooms. The purpose of our study was to conduct a comparative case study and explore how four district leaders promoted CRPs throughout each of their districts. Research Design: Situated in the Midwest, we used a comparative case study to explore the approaches of four Black women school district leaders. Data included a focus group interview with the leaders; four individual, follow-up interviews; and artifacts or documents provided by the leaders. The data collected was analyzed using the Culturally Responsive School Leadership analytical framework. Results and Discussion: Findings discuss school district leadership's responsibility to promote CRPs; district leaders' ability to foster trusting relationships with educators; and district-wide efforts to engage in purposeful teacher retention practices. A discussion and conclusion include implications considering how district leadership can influence the implementation of CRPs in schools and classrooms.