Since 1894, Culver Academies has aimed to develop leaders of character. Rooted in the military academy and boarding school traditions, Culver has centered leadership development around central virtues and values. In 1986, recognizing the need to provide integrated, successive leadership learning experiences for students across 4 years, Culver instituted a standalone academic Department of Leadership Education. The Department of Leadership Education, housed in the Schrage Leadership Center, is unique among secondary boarding schools in offering four successive academic leadership education classroom experiences alongside Student Life curricula. Each year’s curriculum is centered in a transformational leadership framework, utilizing evidence-based tools to guide students’ leadership and character growth at each level. Ultimately, students’ growth is assessed by faculty (and students themselves) according to core leadership and character competencies developed by the Academies. Continual improvement of the department is ensured through a comprehensive triennial review process. The aim of this article is to illustrate a successful, iterative character and leadership education experience in a 4-year secondary school context.