Organized sports are an important context for promoting character, and the particular values emphasized illuminate how a setting develops or reveals character. The Character in Sport Index (CSI), an observer rating scale of sportsmanship in cadets within the United States Military Academy (USMA; 2 samples, n = 1,926 and 1,798) engaged in intramural sports, measured setting-specific character virtues relevant to USMA. Using 12 items, two factors emerged: positive behaviors (e.g., resilience) and negative behaviors (e.g., argumentativeness). The positive behavior factor was related to grit, self-regulation, academic and military achievement, and an instructor-completed character rating scale. The negative behavior factor related to manipulative traits and number of disciplinary reports. Findings are discussed in regard to sportsmanship and character development within USMA and in other college settings.