This paper is based on a study examining the performance on the Iowa Gambling Task (IGT) of a group of male adolescents aged 16-18 years incarcerated at a secure corrections facility located near New York City. At the time of IGT administration, 45% of the study participants had been charged with crimes but not yet sentenced; 55% of the study participants had been sentenced. 61% of the subjects had been charged with having committed violent felonies and 39% of the subjects had been charged with committing non-violent felonies or misdemeanors. In an effort to contextualize the results of the study sample.s performance on the IGT, participant performance was compared to the IGT performance of two groups of adolescents that had never been incarcerated (N = 42, N = 31). Findings demonstrate that the study sample performed significantly worse on the IGT than the community-based samples. Study participant performance was also compared to IGT performance of a group of previously incarcerated adults (N = 25). There was no statistically significant difference in the mean performances of these groups. The study also examined the relationship between antisocial behavior and psychopathic traits and decision-making (as measured by the IGT). No significant differences on IGT performance were identified between study participants charged with committing violent felonies and study participants charged with non-violent felonies and misdemeanors. No association was found between the presence or absence of psychopathic traits, specifically callous-unemotional traits, and IGT performance. Implications for research and practice are considered.