The purpose of this study was to gain a thorough understanding of the high school sport captaincy experience. Thirteen university freshmen (7 males, 6 females) who were high school sport captains the previous year participated in 60—90 min semistructured interviews. Hierarchical content analysis of the data revealed that the majority of participants believed that their captainship experience was positive, but also cited difficult aspects such as having responsibility/being held accountable, being scrutinized/meeting expectations, and staying neutral in conflict situations. The majority of captains also reported receiving little to no training from coaches for their captaincy role and indicated that they learned to lead largely from previous life experiences, such as by observing significant others and learning through trial and error. Results on perceived roles and duties, perceived effectiveness, attitudes toward formal leadership training, and recommendations for future captains are also provided. Implications for designing youth sport leadership development interventions and advancing research on youth leadership are discussed.