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Building on the seminal work of Césaire (2000) and Fanon (2004), this paper places the colonial legacy of educational leadership in conversation with a critical read of its colonial origins while offering a decolonial lens to identify a more critical understanding of the roles of educational leaders and leadership programs in the maintenance of the hegemony of colonization. The author provides historical discourse that paints a picture of the origins of the roles and duties of early educational leaders to identify and name the colonial roots of the profession. Building on this work, this paper brings the colonial history of the field to bear on current educational leadership theories and practices, while also pushing for a deeper analysis of how colonial practices are refashioned and embedded in educational leadership preparation, policy, research and practice. Moving the discussion forward, this paper takes up what Césaire (2000) articulated as “plumbing the depths” (p.43) to begin to reflect upon how leadership preparation programs can create spaces and opportunities to engage and prepare future leaders to imagine critical possibilities while also under the Gaze of the colonial apparatus of Educational Leadership.