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The following research is an examination of a district-level equity leader named Jessica Dawson and her 20-year career of applied equity and culturally responsive leadership. This work explores a new theoretical concept entitled Culturally Responsive District Leadership, which we regard as leaders who systematically examine, repair, and re-conceptualize notions of anti-blackness and cultural differences on a systemic level (district). Moreover this research investigates how equity leaders tasked with leading and improving cultural responsiveness for districts are at times placed in organizational locations of vulnerability. In Jessica’s case she is simultaneously required to advocate for students and lead teacher and staff programs of equity improvement. We see Jessica’s “applied equity work and leadership” as the embodiment of this new theory.