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The current study examined the incremental validity of the Psychopathic Personality Inventory- Revised in relation to the Psychological Inventory of Criminal Thinking Styles and Personality Assessment Inventory in predicting failure of a Residential Drug Abuse Treatment Program among 222 male inmates. Failure was defined as expulsion, withdrawal, or restart of the residential phase of the treatment program or failure during the community transition phase. One-hundred fifty-eight inmates completed the program and 64 failed. Analyses revealed that scales on the Psychopathic Personality Inventory-Revised and the PAI predicted treatment failure with low predictive accuracy that was greater than chance. Specifically, the Psychopathic Personality Inventory-Revised Total score and Rebellious Nonconformity score were predictive of program failure (AUCs = .610 and .602 respectively). In addition, the Fearless Dominance Factor of the Psychopathic Personality Inventory-Revised that was predictive of program failure (AUC = .603, OR = 1.02). Lastly, the Grandiosity subscale of the PAI Mania scale was predictive of program failure (AUC = .605). No scale on the Psychological Inventory of Criminal Thinking Styles was predictive of program failure. Among the scores that were predictive, none emerged with incremental validity over the others. A diagnosis of cocaine dependence was demonstrated the greatest utility in predicting program failure ( OR = 4.15). These findings suggest that treatment outcome may be more associated with the affective and interpersonal facets of psychopathy than with antisocial behavior. Furthermore, findings support previous literature indicating the Fearless Dominance and Self-Centered Impulsivity factors that comprise the Psychopathic Personality Inventory are associated with different characteristics and behavioral outcomes.