Objective: We examined the relationship of socially maladaptive behaviors with decision making and psychopathy in a sample of 26 high-risk males recently released from incarceration who were currently clients in an offender reentry service program. Method: The Iowa Gambling Task (IGT) and the Psychopathy Checklist Revised (PCL-R) provided measures of individual differences in decision making and psychopathy, respectively. Results: The IGT and PCL-R each contributed differentially to specific socially disadvantageous outcomes, with poorer decision-making scores predicting recidivism at 3- to 6-month follow-up, and higher psychopathy linked to a retrospective measure of total lifetime incarceration. In addition, in relation to both nonrecidivist and control groups, recidivists showed a distinct pattern of IGT performance for the last 3 blocks of trials, characterized by a failure to learn from feedback and to modify their preferences to more advantageous decks of cards. In addition, the IGT and PCL-R correlated, with poorer decision making corresponding to higher ratings in psychopathy. Conclusions: The current findings may add to growing evidence of ecological validity of both decision making and psychopathy in relation to real-life outcome measures in high-risk individuals.