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. The Iowa Gambling Task (IGT) and the Psychopathy Checklist Revised (PCL-R) provided measures of individual differences in decision making and psychopathy, respectively. 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. 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.(PsycINFO Database Record (c) 2019 APA, all rights reserved)