Sampling multiple sports in childhood is associated with continued participation in sport, but little is known about whether sport sampling may be associated with youth character development, another outcome of widespread interest in the field. Furthermore, even less is known about how sport participation influences development. For example, sport participation itself may not be what fosters the development of character but, instead, character may be developed though "how" youth engage with sport. Therefore, this study examined associations between sport pathways, levels of task and ego orientation, and character attributes among 445 high school athletes (49% female) in the United States. In adolescent athletes' retrospective reports of participation in 28 different sports from kindergarten through Grade 5, participation patterns had mixed associations with character attributes. Task and ego orientation were stronger predictors of character, suggesting that character is associated less with the pattern of participation and more with the spirit in which that participation occurs. Parents and coaches interested in psychosocial development should therefore attend to fostering young athletes' prosocial engagement with sport regardless of how many sports they play.