This comparative case study of two elementary schools employs Flexible Leadership Theory (FLT) and cultural leadership theories in order to explore how leadership approaches influence student academic success and the prevention of juvenile justice involvement. The researcher used a comparative case study framework in order to contrast two demographicallysimilar elementary schools, which varied greatly in terms of students’ juvenile justice involvement. The researcher interviewed a minimum of six stakeholders per school and used an interview guide to facilitate participant responses. Results of the study indicate that FLT and cultural leadership are present in the two schools studied. Most notably, FLT and culture development regarding the importance of attendance, individual student relationships, and individual response to at-risk behaviors differentiate the two comparison schools. Results also suggest leadership and cultural practices that prevent juvenile justice involvement when other considerations are present.