The authors examined cross-lagged links among gambling, substance use, theft, and violence from midadolescence to young adulthood and whether behavioral disinhibition, deviant peers, and parental supervision as common risk factors explain or moderate those links. In 2 community samples, male Caucasians were assessed for gambling participation and problems with the South Oaks Gambling Screen—Revised for Adolescents (K. C. Winters, R. Stinchfield, & J. Fulkerson, 1993) at age 16 years and the South Oaks Gambling Screen (H. R. Lesieur & S. B. Blume, 1987) at age 23. Other problem behaviors were also assessed both times. Risk factors were measured at age 16. Adolescent substance use was related to subsequent theft and violence but not gambling. Gambling problems were linked to subsequent gambling participation. For adolescents with deviant peers, gambling problems were linked to subsequent theft; this was not the case for adolescents without deviant peers. Only for individuals high on disinhibition did stability of gambling problems resemble moderate stabilities of other problem behaviors. Each risk factor was related to each problem behavior (exception: parenting unrelated to gambling). These risk factors partly explained the cross-lagged links among behaviors and thus may be useful targets of prevention.