Joining a gang increases an adolescent’s risk for substance abuse. To better understand the contextual development of drug use behavior, this retrospective ethnographic study describes a sample of 76 young small-city mainland Puerto-Rican and Dominican males who joined gangs when they were younger. Data is presented and discussed on the drug abuse behavior including their drug using progression and the context in which such use occurs. The young average age of onset 11.2 (sd = 2.6) combined with the rapid progression to more dangerous drugs, which generally occurs within six years, demonstrates the elevated risk associated with small city gang membership. Differences in the patterns of drug use were also found between the English and Spanish speaking groups. The authors discuss the implications of the study findings on the development of interventions. Recommendations address future research possibilities on drug abuse within Latino gangs.