The perpetration of bullying is a significant issue among researchers, policymakers, and the general public. Although researchers have examined the link between bullying and subsequent antisocial behavior, data and methodological limitations have hampered firm conclusions. This study uses longitudinal data from 411 males in the Cambridge Study in Delinquent Development from ages 8 to 56 in order to examine the relationship between adolescent bullying and distinct late middle adulthood trajectories of offending, in which different groups of males follow different offending pathways. Results show that self-reported bullying predicts only certain adult offending trajectories but that the effect becomes insignificant once controls are introduced for childhood risk factors, although this may be due to the small number of the most chronic offenders. Study implications and directions for future research are noted.