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Prior studies indicate that a significant overlap exists between juvenile victim and offending populations. Youth, especially system-involved youth, encounter a range of victimization experiences, participate in a variety of crime, and their experiences of victimization vary in their capacity to induce a criminal response. So far, however, criminologists have paid little attention to holistically examining such variations in the victimization-offending link that influence the prevalence and magnitude of the overlap. In fact, most victim-offender research either depends on global and composite measures of victimization and offending or disproportionately focuses on violence, which neglects the heterogeneity in victimization histories and offending behaviors among victimized youth. To better understand the intra-group variability of the youth victim-offender overlap, a further look into how different victimization events motivate distinct types of offending is needed. This project describes and dissects differences in victimization experiences as a means of understanding variation in subsequent criminal behavior among a high-risk youth sample. Drawing on general strain theory, the current research (1) examines whether prior violent victimization predicts both violent and property offending, (2) compares the independent effects of direct, vicarious (i.e., indirect), and dual violent victimization on offending outcomes, and (3) observes whether these relationships change when information about the frequency, variety, and recency of victimization events is included in the models. Data from the Pathways to Desistance Study, a multi-site, longitudinal examination of serious juvenile offenders from 2000 to 2010, is used. The findings suggest that identifying whether an individual was directly or indirectly exposed to violence, as well as whether such trauma was recent or occurred in multiple different forms, can be useful for improving our predictions of the impacts of victimization on violent and non-violent offending outcomes. Policy and theoretical implications for the victim-offender and strain literature are discussed.