General strain theory has received a fair amount of empirical support and theoretical elaboration over the past several years. Since the introduction of general strain theory, Agnew and others have attempted to increase the comprehensiveness of the processes involved in strain theory. Until recently, the general strain theory literature has ignored what Agnew and associates (Agnew, Brezina, Wright, & Cullen, 2002) argue may be one of the most important conditioning effects of the strain-crime relationship, namely the dispositions or personality traits of the individual experiencing strain. Recently, Agnew and associates (2002) published results from a study examining the conditioning effects of personality traits (i.e., negative emotionality and low constraint) on the strain-delinquency relationship. Their findings indicated that certain personality traits significantly condition the effect of strain on delinquency. Research has suggested that more severe personality and behavioral traits, such as psychopathy, also influence criminality. The present study examined moderating effects of both personality dispositions and psychopathic behavioral features among a sample of 137 youths referred to juvenile diversion by the court system. The results suggest that personality dispositions and psychopathic behavioral features do not significantly moderate the strain-delinquency relationship. In addition, this study conducted ad hoc analyses examining whether or not delinquency significantly increases the likelihood that subsequent strain and delinquency will result (i.e., a state dependence explanation (see Nagin & Farrington, 1992; Nagin & Paternoster, 1991)). Moderating effects of personality and psychopathy were also included in this model. Further, the role of strain as a mediator for the personality and psychopathy link to delinquency was tested. The findings suggest that delinquency exacerbated subsequent strain and delinquency levels among these youths. Personality and psychopathic features did not moderate the strain-delinquency relationship. Strain did not significantly moderate the personality-delinquency relationship. Limitations and implications for future research and policy are discussed.