The current study compares 3 distinct approaches for measuring juvenile psychopathy and their utility for predicting short- and long-term recidivism among a sample of 1,170 serious male juvenile offenders. The assessment approaches compared a clinical interview method (the Psychopathy Checklist: Youth Version [PCL:YV]; Forth, Kosson, & Hare, 2003), a new self-report measure (the Youth Psychopathic Traits Inventory; Andershed, Kerr, Stattin, & Levander, 2002), and a personality-based approach (the NEO Psychopathy Resemblance Index; Lynam & Widiger, 2007). Results indicate a modest overlap between the 3 measures (rs = 0.26-0.36); however, youths were often identified as psychopathic by 1 measure but not by others. Measures were weakly correlated with reoffending during subsequent 6- and 12-month periods. Findings suggest that although such scores may be useful indicators of the need for heightened monitoring in the short term, care should be taken when making predictions about long-term recidivism among adolescents. Moreover, the lack of long-term predictive power for the PCL:YV and the inconsistent psychopathy designations obtained with different measures raise serious questions about the use of such measures as the basis for legal or clinical treatment decisions. (Contains 3 footnotes, 9 tables, and 1 figure.)