Criminal behavior and related disorders have been associated with abnormal neural activity when experiencing or anticipating risks and rewards, as well as when exercising inhibition. However, behavioral and neural substrates of risk preferences and criminality have received scant attention when unconfounded with experience, anticipation, and inhibition. We test predictions of fuzzy-trace theory (FTT) in two experiments using a risky-choice framing task. Behavioral results show that individuals with a greater history of criminal behavior are less likely to engage in simple meaning-based processing and are less confident when doing so. These findings are supported by fMRI results showing a greater history of criminal behavior is associated with increased activation in regions associated with cognitive control when engaging in simple meaning-based processing. These results provide insight into the cognitive processes and brain mechanisms that are associated with criminal behavior.