We aimed to test direct and indirect associations of affective and cognitive empathy and utilitarian judgment (UJ) on involvement in serious crimes during adolescence. An Italian sample including 67 male incarcerated youths and 239 male community youths completed Rule-Breaking (RBS), Perspective Taking (PT), and Empathic Concern (EC) scales. Moreover, participants responded to moral dilemmas evaluating UJs. A community control and a community deviant group were identified based on the scores on RBS. A MANOVA showed that incarcerated youth were higher in UJ and lower in PT than community control youth whereas community deviant group was lower in EC than the other two groups. A Structural Equation Model evidenced that UJ was directly associated with the probability of belonging to the incarcerated versus community control group and mediated the relationship between PT and group. Results were discussed in light of different theoretical explanations of the used measure for UJ.