Purpose Important facets of the association between violent crime victimization and criminal offending remain unsettled. Drawing on key aspects of General Strain Theory, this study examined whether violent crime victimization affects overall offending proclivity as well as the character—violent vs. nonviolent—of criminal behavior. Additionally, it tested a recent theory extension positing that larger effects of violent victimization will be found among individuals with a greater confluence of criminogenic risk factors. Methods Multi-level latent variable item-response models are used to examine data from a sample of nearly 3,000 tenth-grade students from thirty Kentucky counties. Results Quantitative analyses indicated that greater violent victimization was associated with both higher scores on a latent index of overall offending and with an elevated propensity for violent criminality in particular. Contrary to expectations, effects of violent victimization on overall offending and the propensity for violence were not higher for individuals with higher scores on a multidimensional risk index. Conclusion In support of General Strain Theory, violent victimization elevates the overall amount of criminal offending and increases odds that crimes involve violent rather than nonviolent behaviors. However, variations in the preceding effects across levels of criminogenic risk are not consistent with the theory.