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As a Latina educational professional, the researcher has witnessed and heard stories of many talented executive women who have left the profession due to mistrust in both the educational system and the people who “lead” them. Without trust, relationships are broken, and mistrust permeates every interaction (Tschannen-Moran & Hoy, 1998). In light of the researcher’s insider knowledge (Brannick & Coghlan, 2007), this study sought to examine the trust relationship between Latina leaders in the executive cabinet and the superintendent, specifically to examine female perceptions of the superintendent’s behavior, how superintendents build and elicit trust or mistrust with their leadership teams, and how building trust or mistrust potentially hinders female ascension into top superintendent leadership roles.