Preparing students for post-secondary success requires more than content specific academic learning; a growing body of evidence suggests that character development is equally vital. Analysis of the contemporary research reveals common themes in the attributes of resilient individuals, such as communication, problem solving, independence, sense of purpose, and self-reflection, as well as the methodology to develop resilience in students as a teacher or facilitator. These common attributes provide a framework for structuring developmental curriculum for high school students and the Rudder Leadership Team. The purpose of this mixed-method study was to examine resilience and determine if there was an improved resilience level for students who participated in the Rudder Leadership Team at William Smith High School. This research investigated resilience and compared participants of the Rudder Leadership Team students with the rest of the high school student body. It further analyzed the aspects of the program that could impact current leadership students and alumni of the program. The results show a significant increase in the resiliency levels of leadership team members. The research also suggests specific recommendations to continue certain aspects of the program and to change others.