Rumination, a perseverative cognitive process that involves repetitively and passively focusing on negative emotions, is a transdiagnostic risk factor for the development of psychopathology. Although rumination has been linked to various forms of psychopathology including depression, anxiety, and alcohol misuse, little is known about the conditions that lead to multifinality. Here, we test putative moderators (Nolen-Hoeksema & Watkins, 2011) of the association between rumination and subsequent internalizing symptoms and frequency of alcohol use during adolescence. Participants included 388 youth (52% girls; 90% Caucasian) in a longitudinal birth cohort study who completed questionnaires in Grades 9 and 11. Brooding, a maladaptive form of rumination measured in Grade 9, was associated with greater internalizing symptoms in Grade 11 and greater perceived peer rejection in Grade 9 amplified this association. Brooding was also associated with greater frequency of alcohol use among adolescents who reported having more friends who use alcohol. Gender differences were also examined. Findings provide support for some of the predictions regarding moderators of multifinality made by Nolen-Hoeksema and Watkins. Implications of understanding divergent trajectories in the prevention of psychopathology are discussed.