The “successful psychopath” is thought to evade scientific study because most forensic psychopathy research is limited to incarcerated—putatively unsuccessful—samples. By redefining criminal success as the proportion of past undetected crimes, the present study tested the hypothesis that psychopathic traits are associated with criminal success within an incarcerated sample ( N = 307). Psychopathy was assessed using the Hare Psychopathy Checklist–Revised. Criminal history was assessed retrospectively for 24 violent and nonviolent crimes via self-report using a confidential semistructured interview. Controlling for social desirability score, greatest criminal success was associated with moderate to high psychopathy scores, particularly for violent crimes. At the trait level, antisocial lifestyle and behavioral psychopathic traits predicted increased criminal success, whereas affective psychopathic traits predicted decreased criminal success. These results suggest that criminal success can be meaningfully evaluated using an incarcerated sample and can inform models of psychopathy.