A growing body of research shows that principal turnover is higher among people of racialized backgrounds (Meyer et al, 2020), associated with lower rates of student proficiency (Grissom & Bartanen, 2021) and most often is due to environmental conditions (Levin, Bradley & Scott, 2019). In partnership with the San Francisco Unified School District, I sought to explore the tenure experiences of their Black school leaders. I conducted 20 semi-structured interviews with African American principals and assistant principals. I combine social cognitive framework about administrator career decisions (Fairley-Ripple et al, 2012) with critical organizational theory (Ray, 2019) to demonstrate how SFUSD operates as a racialized organization despite espoused district commitments to African American students, Black educators and antiracist pedagogy. By looking at the district's new leader induction program, I show that there are unintended consequences to their efforts. For example, through helping new principals and assistant principals to name, interrogate and challenge unjust systems, Black leaders are more aware of the ways in which white supremacy culture is negatively impacting their work. [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.]