Using the Psychopathy Checklist-Revised (PCL-R; R. D. Hare, 1991) diagnostic cut-off score of 30, the complete criminal career and community release profiles of 317 Canadian federal offenders (224 low scorers and 93 scoring within the psychopathic range) were investigated. Adult crimes were coded according to age at commission as well as either violent, nonviolent, or nonsexually violent. Changes in performance following release into the community also were examined. Results indicated that offenders scoring within the psychopathic range consistently committed more violent and nonviolent crimes than their counterparts for about three decades, spanning their late adolescence to their late 40s. Numbers of nonviolent criminal offenses committed by high PCL-R scorers declined considerably after age 30 relative to violent offenses, which declined and then rebounded in the late 30s before a major reduction was evidenced. Throughout adulthood, high PCL-R scorers failed during community release significantly faster than did low scorers. Importantly, from a risk management perspective, the release performance of low PCL-R scorers improved with age, whereas the opposite was seen for high scorers. Further, offenders scoring high on the PCL-R did not show a lower charge to conviction ratio with age, suggesting that they may not have been getting better at manipulating the legal system.