Purpose: Criminal career research has recently found that symptoms of psychopathy are more prevalent among offenders following chronic offending trajectories. In the current study, the ability of psychopathy to predict involvement in chronic offending trajectories above other criminogenic risk factors was examined. Methods: Criminal convictions were measured for Canadian male (n = 262) and female (n = 64) offenders at each year between ages 12 and 28. Semi-parametric group-based modeling identified four unique trajectories labeled bell-shape offenders (27.9% of sample), slow desisters (28.5%), slow rising chronic offenders (19.0%), and high rate chronic offenders (24.5%). Results: The four and three factor model of the PCL: YV were associated with the most chronic and serious offending trajectory even after controlling for a variety of relevant criminogenic risk factors. Self-reported involvement in weekly physical fights was a significant predictor of trajectory group membership, but most criminogenic risk factors were more informative of the strength of the relationship between higher symptoms of psychopathy and offending trajectories than of a direct effect of a specific risk factor on the unfolding of offending. Conclusions: Interpersonal and affective symptoms of psychopathy were not related to chronic offending. Future research should examine whether these symptoms are related specifically to involvement in violent offending.