Exposure to violence (ETV) has emerged as a key and stable predictor of violent offending. However, not all youth offenders who experience ETV go on to chronic violent offending. Consequently, it is possible that individual differences, such as psychopathic traits, may be an important factor in the link between ETV and violent offending. These traits are associated with exposure to violence and, separately, to violent offending. The present study used data from Pathways to Desistance, a multisite, longitudinal study of serious juvenile offenders (N = 1170, Meanage = 16.05, SD = 1.16) to explore these relationships, simultaneously. First, autoregressive cross-lagged path models were used to examine the longitudinal bivariate relations among violent offending, ETV, and psychopathic traits. Second, latent class growth analysis was used to determine trajectories ETV. And third, the mediating influence of psychopathic traits was examined. Results indicated that ETV predicted later engagement in violence, but there was some degree of reciprocity between ETV and violence over time. Additionally, respondents with stable high or increasing trajectories of ETV reported more instances of violent offending. Finally, psychopathic traits mediated the relationship between ETV and violent offending. Together these findings support the notion that individuals with psychopathic traits perceive and internalize their environment differently than others and that this difference guides their own violent offending. Given the importance of psychopathic traits for understanding the influence of ETV on violent offending, prevention and intervention strategies must be developed that take into account both individual differences and environmental factors.