Psychopathy has traditionally been viewed as a two-factor construct composed of core personality and antisocial features. This two-factor model was called into question by Cooke and Michie. Specifically, Cooke and Michie proposed a three-factor model that divided the original first factor into interpersonal and affective factors. The traditional second factor was reduced to only including irresponsible and impulsive behaviors, thereby deemphasizing antisocial characteristics. Recently, Hare found evidence of a four-factor model that reincorporates antisocial items. The current study examined two-, three-, and four-factor structures in adolescent offenders (IV = 130) via confirmatory factor analyses. The results suggest that the two-factor model was a poor fit; however, three- and four-factor models evidenced good fit and were justifiable. These findings have important implications for the construct validity of the Psychopathy Checklist: Youth Version. Implications for potential developmental trajectories, dangerousness, and treatment are discussed.