In the present study, the structural validity of the dutch version of the psychopathy checklist: youth version (in dutch: psychopathie checklist: jeugd versie; pcl:yv; de ruiter, kuin, de vries, & das, 2002) was examined in adolescent offenders by means of confirmatory factor analysis (cfa) and item response theory (irt). The pcl:yv item ratings for 269 adolescent males, either admitted to a dutch juvenile treatment institution or psychologically evaluated upon request of the court, were used to test the fit of different factor models presumed to represent the structure of psychopathy as measured by the pcl-r in adults. The study provides support for a good absolute and relative fit for the 3-factor model, but not for the 4-factor model. Results from irt analyses demonstrate the highest discriminative value for the affective items in the dutch adolescent sample. The present findings demonstrate poor discriminative power and age influence on item functioning for most antisocial items of the fourth factor.