The association between psychopathy and crime is established, but the specific components of the personality disorders that most contribute to crime are largely unknown. Drawing on data from 723 confined delinquents in Missouri, the present study delved into the eight subscales of the Psychopathic Personality Inventory–Short Form to empirically assess the specific aspects of the disorder that are most responsible for explaining variation in career delinquency. Blame externalization emerged as the strongest predictor of career delinquency in ordinary least squares regression, logistic regression, and t-test models. Fearlessness and carefree nonplanfulness were also significant in all models. Other features of psychopathy, such as stress immunity, social potency, and coldheartedness were weakly and inconsistently predictive of career delinquency. Implications of these findings for the study of psychopathy and delinquent careers are discussed in this article.