In recent years, the delinquent behaviors related to misbehavior of adolescents have been on the rise and emerged as various social issues, including criminal behaviors. More importantly, these antisocial behaviors of adolescents may lead to serious pathological phenomena and criminal behaviors when they reach adulthood. As such, delinquent behaviors of adolescents can be negatively interpreted as they can do harm to others as well as themselves. However, Winnicott interprets these antisocial behaviors as positive and considers them a sign of hope. In this line, this study attempted to investigate the antisocial tendencies of adolescents in the perspective of ‘hope’, focusing on the Object Relation Theory of Winnicott. To this end, this study employed a case study methodology. Two teenage visitors were selected as the participants of the study. It was found that the antisocial behaviors in adolescence can be positively interpreted, which in turn can lead to a hope. The settings of Christian counseling should be a space where a good environment is provided, based on the understanding of Winnicott’s antisocial tendencies. In addition, the provision of the God’ ‘holding’ environment to adolescents with antisocial tendencies is expected to create a holistic therapy and recovery.