This study compared how normative personality dimensions of the Five-Factor Model (FFM) and neurobehavioral traits of the triarchic model relate to psychopathic tendencies and clinical outcomes in an incarcerated sample of 277 Italian male offenders. Associations between triarchic model traits, measured using the TriPM and the FFM dimensions, measured using the NEO-FFI, were consistent with prior studies. Scores on the TriPM, particularly the Disinhibition scale, were associated with substance abuse and self-harm behavior over and above the presence of psychopathy, and beyond the personality dimensions indexed by the NEO-FFI. By contrast, the Neuroticism and Extraversion scales showed incremental validity, over and above psychopathy and TriPM scores, in predicting depressive tendencies. Lastly, both NEO-FFI and TriPM scales contributed to prediction of staff ratings of behavior in prison and prognosis for release, above and beyond psychopathy. These findings highlight potential advantages of the FFM and triarchic trait models for predicting clinical outcomes.