Callous-unemotional (CU) traits, conduct problems (CP), and deficits in executive control are all linked to the development of more severe antisocial behavior, including violence and substance use. Though previous research has examined the impact of these factors on antisocial outcomes, little work has examined trajectories of CU traits across adolescence and how these trajectories predict greater antisocial behavior in adulthood. Moreover, no study has assessed how severity of early CP and executive control may exacerbate these pathways and increase risk for later violence and substance use. The current study (a) identified trajectories of CU traits among a large, high-risk sample of adolescent males, (b) examined the relationship between CU traits trajectories and future violence and substance use, and (c) examined whether early CP and executive control moderated the effects of a high CU traits trajectory membership and high CP on violence and substance use. Results indicated that: (a) CU traits could be grouped into three stable trajectories across adolescence, (b) the 'high' CU traits trajectory, particularly in the presence of 'elevated' CP, was related to higher violence and substance use, over and above a variety of environmental risk factors, and (c) the effects the 'high' CU traits trajectory on both violence and substance and in the presence of 'elevated' CP was stronger among youth with high executive control. These findings highlight the utility of identifying subgroups of youth who differ on trajectories of CU traits for understanding the development and maintenance of severe antisocial behavior.