The analysis of the intertwining of individual and collective life trajectories has a dynamic, complex, and differentiated vision. In this context, our research objective was to describe the life trajectories (family, personal and group) of young offenders who are deprived of liberty in Maule, Chile. We opted for a case study design with the participation of six young people, who responded to semi-structured interviews based on theoretical categories. This information was complemented with content analysis of the Individual Intervention Programs provided by the National Minors Service (SENAME). The results show the youth itineraries modeled by histories of exclusion, abandonment, and violence, as well as the failure of a judicial system 15 years after the implementation of Law 20.084 of the Ministry of Justice. The revision of social reinsertion programs, the installation of a monitoring and evaluation system in the external environment and the implementation of mental health programs in the SENAME centers are pending tasks.