Using a novel quantitative model of repeated choice behavior, we investigated the cognitive processes of criminal offenders incarcerated for various crimes. Eighty-one criminals, including violent offenders, drug and sex offenders, drivers operating a vehicle while impaired, and 18 matched controls were tested. The results were also contrasted with those obtained from neurological patients with focal brain lesions in the orbitofrontal cortex and from drug abusers. Participants performed the computerized version of the Iowa gambling task (Bechara, Damasio, Damasio, & Anderson, 1994), and the results were decomposed into specific component processes, using the expectancy valence model (Busemeyer & Stout, 2002). The findings indicated that whereas all the criminal groups tended to select disadvantageously, the cognitive profiles exhibited by different groups were considerably different. Certain subpopulations—most significantly, drug and sex offenders—overweighted potential gains as compared with losses, similar to chronic cocaine abusers. In contrast, assault/murder criminals tended to make less consistent choices and to focus on immediate outcomes and, in these respects, were more similar to patients with orbitofrontal damage. The present cognitive model provides a novel way for building a bridge between cognitive neuroscience and complex human behaviors.