Urban high schools that predominantly service at-risk students have not been faring well, with disproportionate numbers of minority children and poor White children are dropping out. The purpose of this mixed methods study was to examine the relationship between leaders' successes and the number of reduced dropout initiatives in 2 urban schools. This research was guided by empirical literature that included a review of various successful leadership practices. Case study interviews were conducted with 2 principals and 3 directors and were analyzed for common themes. Quantitative survey data were collected from a purposeful sample of 195 students and 7 administrative leaders in these schools; these quantitative data were then analyzed via descriptive statistics. Findings from the interviews indicated that multiple styles of leadership (e.g., distributive, transformational) are recommended as critical in these complex environments. Findings from the quantitative surveys indicated that students appreciated the role of management and the need for increased engagement in school. Administrators indicated a need for upper management support. This study contributes to social and organizational change by providing stakeholders with a better understanding of how management indirectly influences reduced dropout of at-risk youth. Future studies should include parent voices as they relate to high school dropout and connectedness to schools.