Although there is a documented link between psychopathy and instrumental violence in adult offenders, the association between these constructs has not garnered significant attention in adolescent offenders. In this study, we evaluated the relationship between psychopathy and instrumental aggression in a sample of 122 male adolescents incarcerated in a state facility for serious and chronic offenders. We evaluated the primary (2-, 3-, and 4-factor) models of the Psychopathy Checklist: Youth Version (PCL:YV; Forth, Kosson, & Hare, 2003) and assessed their relationship to a separate 5-item measure of instrumental violence. CFA revealed good model fit for the 3- and 4-factor latent variable models of adolescent psychopathy and a single-factor model reflecting a 5-item measure of instrumental violence. Structural equation modeling results indicate that the 4-factor model accounted for 20% of the variance for instrumental violence. In contrast, the 3-factor model of the PCL:YV accounted for 8%, and the 2-factor model accounted for 5% of the variance associated with instrumental violence.