Research in the field of developmental psycho-criminology shows that conduct disorders and deviant behaviours are frequently associated with traumatic and adverse developmental experiences. Personality traits and psychopathological symptoms also increase the risk of criminality. However, the role of psychopathological symptoms in the relationship between adverse childhood experiences and offending has rarely been researched. The present study was designed to throw further light on these issues by analysing risk factors in a group of adolescents and young adults in a juvenile detention centre in southern Italy. Results support the idea that the accumulation of risk factors is a major factor in recidivism and highlight the key role played by the contexts and emotional environments in which children and adolescents grow up. They also underline the link between paternal antipathy and hostile behaviours and the potential impact of paternal antipathy and hostility on triggering delinquent trajectories. Our study’s main limitations are its small sample size and the absence of longitudinal measures. Nevertheless, combining detailed measures of a wide variety of factors with risk assessments drawn up by professionals who work with young offenders provided insights into the most suitable interventions for young delinquents. More precisely, because young offenders are victims of adverse childhood experiences as well as perpetrators of delinquent acts, interventions aimed at changing their life courses must adopt a global perspective that encompasses both their personal characteristics and their family circumstances, in order to provide an external environment conducive to non-recidivism.