A paucity of literature exists on the processes of character development within diverse contexts. In this article, the authors use the United States Military Academy at West Point (USMA) as a sample case for understanding character development processes within an institution of higher education. The authors present a discussion of relational developmental systems theories and relevant research areas that might be leveraged to promote the positive character development goals of USMA. They conclude with the implications of this work for informing character development research and education in other settings, including non-military institutions of higher education.