Tools for measuring psychopathy have been widely used as predictive assessments of future violence and antisocial behavior in correctional settings. Yet, research concerning juvenile psychopathy has yielded mixed conclusions as to its use as a long-term predictive measure of future psychopathy and offending in adulthood. The current study assesses the predictive utility of both the Psychopathy Checklist – Youth Version (PCL-YV) and the Youth Psychopathic Traits Inventory (YPI) on subsequent psychopathic traits, self-reported offending, and arrests across seven key years of development. This study used data from Pathways to Desistance, a longitudinal study of 1,170 male youth adjudicated for a serious crime (aged 14-17 at baseline; M = 16.6). PCL-YV and YPI total scores at the first study follow up predicted YPI total scores at every following study time point, up to 6.5 years later (Betas ranged from .311-.680, p-values ranged from <.01 to < .001). Descriptively, though, YPI scores declined over time (M = 109.8 at 6 months; M = 100.2 at 7 years). PCL-YV and YPI scores predicted subsequent offending behavior consistently for 2.5 years only (Betas ranged from .007-.031, p-values ranged from <.01 to < .001), while official arrests were not consistently predictive for any time period. While short-term predictive utility of juvenile psychopathy measures was evidenced, these findings call into question whether psychopathic traits measured in adolescence should be used to make predictions about long-term recidivism risk, especially across developmental periods.