Data were collected for 1998 middle/high-school students in Ontario to assess involvement in gambling, substance use, and generalized risky behavior. To predict these outcomes, measures for anxiety, family cohesion, and coping style were also administered. Three a-priori models were posited to account for the impact of risk factors, protective factors, and combined risk/protective factors on the development of risky behaviors. A high-risk cohort composed of subjects endorsing at least one risky behavior (gambling, substance use, or generalized risky behavior) within the clinical range was created to test an unobserved outcome variable created from all three measures of risky behavior, which was successfully predicted by two of the three a-priori models. Implications for the inclusion of gambling within a constellation of high-risk behaviors and recommendations for future prevention efforts are discussed.