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In this paper, we draw from nearly a decade of primary research and partnership work with leaders in U.S. school districts to explore the politicization of equity and justice leadership work through times of political change (Dixson, 2018; Irby and Ishimaru, 2025; Ishimaru, Irby, and Green, 2022). To answer the question “What are the local and national racial-historical contexts that influence leaders to take up particular equity leadership approaches within local school systems?” we draw central findings from a multi-year case study that explored leadership activities and outcomes in three school districts during Obama, Biden, and Trump eras. Our submission advances Division L’s priority to analyze how historical legacies, community histories, and sociopolitical conditions inform contemporary educational priorities and challenges.