Testing the indirect effect of psychopathic personality towards recidivism has been one of the overlooked areas within criminological studies. Based on this fact, the current study articulated the mediated effect of psychopathic personality towards recidivism against criminality attitude, knowledge on criminality, prison syndrome, social exclusion, peer influence and drug abuse as premeditated factors. One-hundred and ninety-six adult offenders with repeated criminal records since three years later participated in the semi-structured interview. Structural Equation Modelling conferred drug abuse, associate influence, and social exclusions had indirect effect on recidivism through psychopathic personality. Yet, knowledge on criminality and drug abuse was partially mediated by psychopathic personality. Implications for crime prevention and reduction are discussed from the lens of policy and practice strategies.