A case study of a high school ice hockey program designed to teach players life skills and values was conducted to understand, from the perspective of administrators, coaches, parents, and players, the strengths and challenges of the program. Results indicated that the program’s strengths lied in its comprehensive approach to teaching life skills and values in addition to coaches’ ability to foster relationship with players. However, program members also faced many challenges related to traveling, a lack of resources, and conflicting goals. Results are discussed using the Petitpas et al. (2005) framework and the youth development through sport literature.