In most social and behavioral science theories, depictions of ordinary criminals tend to ignore the emotional states of offenders and the possible relationship between emotionality and criminal behavior. Theorists who do consider emotions tend to presume that crime is motivated by subconscious desires to remove guilt by being punished. This paper challenges this presumption using evidence from life-history data on criminal careers. We argue that the failure to consider the emotions of offenders leads to simplistic explanations of criminal behavior. Ordinary property offenders actually experience a great deal of emotional ambivalence concerning crime. By ambivalence we mean that despite appearent social and emotional satisfactions gained from crime, most offenders experience guilt or an enduring sense of shame.