Interactive and mediating effects have the ability to elucidate variable relationships. The goal of the current study was to explore how these two effects potentially clarify the victimization-offending relationship. Examining three waves of longitudinal data, it was predicted that Wave 1 victimization would enhance Wave 2 cognitive impulsivity, Wave 2 victimization would interact with Wave 2 cognitive impulsivity, and Wave 2 cognitive impulsivity and the victimization x cognitive impulsivity interaction would both fuel a rise in Wave 3 delinquency. All predicted relationships were observed when evaluated in a group of 960 early adolescents (457 boys, 503 girls) from the Illinois Study of Bullying and Sexual Violence (ISBSV). When cognitive insensitivity replaced cognitive impulsivity as the mediator, the mediating and moderating effects were no longer significant. These results suggest that victimization stimulates reckless thinking, which, when aided by subsequent victimization, encourages future delinquency.