In this article, we expand and test several theoretical models addressing the longitudinal relationships between bully victimization, depression, academic achievement, and problematic drinking from 3 approaches: Interpersonal risk model, symptom driven model, and a transactional model. Unfortunately, prior research has failed to consider these associations at the within-person level, which is arguably a more relevant level of analysis. Participants were 1,875 students sampled from four Midwestern middle schools and followed for 2 years. Baseline age ranged from 11–13 years with a racially diverse sample (44.3% African American, 29.2% White, 7% Hispanic, 3% Asian/Pacific Islander, and 16.5% Multi-Racial). The current study used an auto-regressive latent trajectory with structured residuals (ALT-SR) model to examine the within-person cross-lagged associations between bully victimization, depression, academic achievement, and problematic drinking. Results indicated support for an interpersonal risk model, where experiences of early bullying victimization resulted in a cascade of problems throughout middle school. Within this interpersonal risk model we also established that academic achievement was a key mechanism linking bully victimization to problematic drinking during adolescence We did not find evidence for a traditional symptom driven model (e.g., stemming from depression); however, we did find long-term problems stemming from early problematic drinking. Results are discussed in relation to prevention interventions for problematic drinking as well as screenings for early adolescent depression, bully victimization, and academic problems.