Scholars of transformational leadership literature assert that school-based management teams are a vital component in transforming schools. Many of these works focus heavily on the roles of principals and teachers, ignoring the contribution of Assistant Principals (APs). More attention is now being given to the unique role that Assistant Principals play in school leadership teams (see for example, Muijs & Harris, 2002). While there is a good amount of literature on what APs do in terms of their roles and responsibilities, what remains unclear; is how and why they enact their role in particular ways, especially under the umbrella of urban school reform. This work will address this gap by examining: how Urban High School Assistant Principals come to understand their role as both leader and staff, particularly in the context of transformational models of leadership? Guided by the theoretical framework of middle management, this study utilized a qualitative case study approach to interview seven Assistant Principals in three urban high schools in a large Northeast coast school district. Additionally, a one-time 15 minute interview with the principals and direct reports to the APs was employed to gain a better understanding of the leadership dynamic within the schools. The interviews were transcribed and coded by the researcher using Atlas.Ti. Through the lens of middle management theory, this work focused on a specific group of Assistant Principals working under a distributed leadership model. The findings revealed that the role of the AP is nebulous position that when not appropriately defined can cause professional difficulties that impede the leadership capacity of APs and the growth of school success. As such, stakeholders involved in schooling need to gain a greater understanding of the psychological and sociological underpinnings that impact the functionality of their middle leaders (those not operating in senior level positions). The findings of this work speak to the intricacies of the Assistant Principalship and contribute to a growing body of literature centered on how Assistant Principals navigate their space as leader and staff in an educational setting where leadership is more shared and collaborative. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]