The third pillar of No Child Left Behind emphasizes determining which educational programs and practices have been proven effective through rigorous scientific research. This study addressed Davis, Darling-Hammond, LaPointe, and Meyerson's (2005) call for a "need for additional research to determine the impact and relative importance of leadership in such key areas as curriculum, assessment, and adaptation to local contexts" (p. 1). Through the lens of authentic leadership, as defined by Avolio and colleagues (Avolio, 2007; Avolio, Gardner, & Walumbwa, 2007; Avolio, Gardner, Walumbwa, Luthans, & May, 2004; Avolio & Luthans, 2006), the decisions made by a deputy superintendent to increase achievement gains and close the achievement gap in her large urban district were examined. Given the relevance and importance of authentic leaders who, as Darling- Hammond, LaPointe, Meyerson, and Orr (2007a) determined, "understand instruction and can develop the capacities for teachers and of schools are key to improving educational outcomes for all students" (p. 1), this study seemed timely. Reform efforts call for maintaining a strong commitment to accountability and flexibility for states and districts, with the assurance that "every classroom in every school is a place of high expectations and high performance" (Duncan, 2011, p.1). As states increasingly request waivers from key provisions of No Child Left Behind, committed, focused, authentic character in action is critical to the goal of closing gaps in achievement and increasing student achievement for all students.