Youth gang affiliation is an emerging problem throughout the world. In Italian context, such phenomenon displays heterogeneous characteristics and motivations which varies regionally due to social and cultural differences. In Northern Italy, where industrialization and immigration are high, gangs mainly attract young immigrants struggling with integration. In Southern Italy, gang membership often involves local youth seeking to elevate their criminal status through ties with established organized crime. These “baby gangsters” share symbols, codes, and behaviors with adult criminal groups, contributing significantly to delinquency and violence. Drawing on Thornberry et al.’s ecological framework, we investigated in community and incarcerated samples potential individual-(i.e., self-serving cognitive distortions), family- (i.e., parental monitoring and acceptance-rejection), and community-levels (i.e., neighborhood violence exposure) risk factors associated with youth gang affiliation. Findings show that gang membership was not related to dysfunctional familyrelationships whereas both self-serving cognitive distortions and being exposed to community violence promote joining a gang. Finally, our longitudinalevidences support the facilitation model highlighting that gang involvement acts as an enhancer, exacerbating antisocial tendencies beyond what could beexplained by cross-sectional associations. Understanding these dynamics is vital for developing effective prevention strategies against youth gang violence in Italy.