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This study investigates the influence of system-involved history and inflated self-esteem on the number of petitions received by youth. Despite ongoing debates regarding the impact of self-esteem on delinquency, empirical research specifically examining inflated self-esteem is limited. This research uses labeling theory, which suggests that youth with a history of system involvement may experience stigma leading to further delinquent behavior. The study employs stepwise regression analysis to explore the interaction between system involvement and inflated self-esteem. The sample consists of youth who have undergone risk assessments within the juvenile justice system. It is hypothesized that there will be a significant positive association between a history of system involvement and the number of petitions. Additionally, it is hypothesized that an interaction effect between system-involved history and inflated self-esteem will be identified. These hypotheses underscore the importance of addressing both labeling effects and the complex role of self-esteem in interventions aimed at reducing delinquency among youth.