The construct of Machiavellianism has been questioned; however, research has largely relied on using the Mach-IV scale within community and student samples. The current study used an incarcerated sample (N = 184) to compare alternative measures of Machiavellianism, assess associations between Machiavellianism and psychopathy, and evaluate the utility of Machiavellianism in predicting criminal history. Alternative Machiavellianism measures were moderately associated with the Mach-IV, modestly associated with psychopathic traits, and accounted for little variance in psychopathy scores. Contrary to prior research, Machiavellianism demonstrated the strongest association with the affective component of psychopathy. Finally, Machiavellianism did not significantly augment predictions of arrests over psychopathy. Future research should replicate these findings in larger forensic samples and explore associations between Machiavellianism and non-forensic outcomes.