The following case study (Stake, 2000) explores the collective properties of the group of leaders working together to enact instructional change in an urban high school (Spillane, et al., 2001). It documents how an urban public high continues to work toward developing and enacting a model of leadership that is transformational, distributed, and democratic and the challenges and successes it has encountered as it struggles to establish such leadership in the context of educational reform which by nature is transactional. The subsequent discussion applies the characteristics of transactional leadership to educational reform, identifies several characteristics of effective urban school leadership, documents the evolution of collective leadership in one urban high school, and asserts that the transactional framework of systemic leadership necessitates school leadership that is collective, democratic, and comprehensive in its breadth of interdependence (Gronn, 2003) if instructional transformation is to occur. (Contains 1 note.)