The aim of the present study was to investigate if interaction effects among Youth Psychopathic Traits Inventory (YPI) Grandiose-Manipulative (GM), Callous-Unemotional (CU), and Impulsive-Irresponsible (II) may add significant information in predicting self-reports of juvenile delinquent behavior among adolescents. A sample of 558 Italian high school students were administered the YPI and the Self-Reports of Delinquency Scale (SRDS) in order to evaluate interaction effects among YPI GM, CU, and II dimensions. Results showed a significant effect for a three-way interaction among the three YPI dimensions in predicting the SRDS total score, beta = .19, p < .01. In conclusion, the findings seem to underline that a three-factor model of psychopathy may help clinicians and researchers in predicting self-reported delinquency better than the individual factors.