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The construct of psychopathy holds promise as a discriminating variable in the classification and explanation of childhood antisocial behavior. The new generation of psychopathy measures, designed to measure this construct in adolescent populations, must meet acceptable standards of reliability and validity prior to the clinical application of the construct with adolescent offenders. The purpose of this study is to examine the construct and predictive validity of adolescent psychopathy as measured by the PCL:YV, PSD, SALE, and SRP-II. Data from two samples of detained adolescent offenders (short-term and long-term detention) are utilized to investigate construct validity via MTMM. In addition, external validity indices including institutional violations (fighting, seclusions, and treatment refusals) and community supervision (probation contacts, drug testing, and re-arrests) are operationalized and measured in order to examine the predictive validity of adolescent psychopathy. Results of construct validity offer modest support for the two-factor model of psychopathy. For external validity, Factor 2 accounted for greater variance in the prediction of institutional infractions and subsequent placements in a secure facility; however, its overall predictive validity was low. The results suggest that the current measures assess psychopathic traits and behaviors which may be stable in adults but are likely to be normative and transient in many adolescents.