Ninety percent of American youth participate in some form of organized youth sport between the ages of 5 and 18. Parent involvement in this context has recently been characterized as a potentially harmful force in parent–child relations, leading to debate regarding the appropriateness and level of parent involvement in organized youth sport. Despite the rising costs associated with youth sport participation, little empirical effort has been made to examine the potential impact of family financial investment on parent involvement and children's subsequent sport outcomes. The purpose of this study was to address how family financial investment in youth sport influences children's perceptions of parent pressure, sport enjoyment, and commitment to continued participation. Data from a national sample of 163 parent–child dyads illuminated an inverse association between family financial investment and child sport commitment, mediated by children's perceptions of parent pressure and sport enjoyment. The results indicated that family financial investment predicts child commitment through the sequential mediators of perceived parent pressure and child enjoyment. These findings draw attention to many avenues for future research on the potential link among family investment decisions, parent involvement behaviors, and child outcomes in organized youth sport, which may collectively inform the development of parent interventions for youth sport leagues, administrators, and parents.