Reckless behavior by business leaders can be a systemic risk for individual firms and the economies in which the firms exist. We propose that a synthesis of behavioral economics, in particular prospect theory, and the study of psychopathy may help researchers better understand why some business leaders engage in high-risk criminal activity. We propose that psychopathy is associated with an abnormal response to negative consequences. Where traditional Prospect Theory proposes that people are loss avoidant, we propose that people high on the trait of psychopathy may be more motivated by gains and will be risk seeking in high reward/high risk situations for which most people will avoid risk. We propose two empirical study designs that may be used to test the framework in the future.