The Great Mountain High School (GMHS) started a program to help support students at risk for not graduating high school. The focus of this study was to provide a formative program evaluation of the created program that (a) investigated the fidelity of implementation of the activities and processes of the program, (b) gathered an understanding of the success of the program's impact on graduation rates, and (c) provided an understanding of the strengths and areas of growth the Leadership Academy. A mixed methods, context, inputs, process, and product (CIPP) evaluation model, with a pragmatic lens, was used during an analysis of a historic document review, teacher interviews, and student participant surveys. I found that (a) the academic components of the program were being implemented with fidelity and the community, and career components were partially implemented with fidelity when compared to the program's design; (b) there was no statistical difference between student participants of the program and similar student non-participants, and (c) the success of the Leadership Academy occurred in the value added to the student and student's perceptions of their life and life after high school graduation. Evidence suggested that the program should continue to be implemented not because of its graduation success but because of the value added to student participants. Further recommendations from this study called for a greater implementation of community-based and leadership-based lessons to increase the fidelity of implementation and more planning time for teachers of student participants to collaborate on more cohesive initiatives. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]