This study examined the role of adaptation in the first year of middle school (Grade 6, age 11) to affiliation with gangs by the last year of middle school (Grade 8, age 13). The sample consisted of 714 European American (EA) and African American (AA) boys and girls. Specifically, academic grades, reports of antisocial behavior, and peer relations in 6th grade were used to predict multiple measures of gang involvement by 8th grade. The multiple measures of gang involvement included self-, peer, teacher, and counselor reports. Unexpectedly, self-report measures of gang involvement did not correlate highly with peer and school staff reports. The results, however, were similar for other and self-report measures of gang involvement. Mean level analyses revealed statistically reliable differences in 8th-grade gang involvement as a function of the youth gender and ethnicity. Structural equation prediction models revealed that peer nominations of rejection, acceptance, academic failure, and antisocial behavior were predictive of gang involvement for most youth. These findings suggest that the youth level of problem behavior and the school ecology (e.g., peer rejection, school failure) require attention in the design of interventions to prevent the formation of gangs among high-risk young adolescents.