This study’s purpose was to examine the relations among future orientation, self-esteem, and later adolescent risk behaviors, and to compare two mediational models involving self-esteem versus future orientation as mediators. An ethnically diverse sample of 12- to 14-year-olds (N = 862, 54% female, 53% ethnic minority) was assessed longitudinally. Correlations supported the hypotheses that future orientation and self-esteem are (a) positively correlated with each other (r > .40) and (b) negatively related to various risky behaviors that were composited into a measure of risk orientation. Controlling for social desirability, self-esteem partially mediated the relation between future orientation and later risk orientation, and future orientation partially mediated the relation between self-esteem and risk orientation. The results shed light on how the concept of possible selves might factor into adolescents’ risk avoidance. In particular, both future orientation and healthy self-esteem may serve as protective factors against engaging in risky behavior.