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This qualitative study examines how school leaders in an urban school district in the Western United States implement the Black Student Excellence Initiative (BSEI), a districtwide strategy aimed at improving the educational experiences and outcomes of Black students. Grounded in transformative leadership theory (Shields, 2010), the study explores how leaders at three school sites—an elementary, middle, and high school—understand the needs of Black students, enact their roles within BSEI, and navigate implementation. Using a multiple-case study design (Merriam, 2009; Yin, 2005), data were collected through semi-structured interviews with six administrators over a two-year period. Findings highlight how the leaders’ identities and experiences, leadership styles, and school contexts influenced their approach to the equity driven initiative.