Tracheobronchomalacia (TBM) is characterized by weakness of cartilaginous supporting structures of tracheal and bronchial walls, resulting in central airway obstruction. It is a rare condition that can occur after prolonged intubation. Here, we report a 26-year-old, alcoholic male who had TBM, mild subglottic, and severe tracheal stenosis following 2 weeks of intubation. Subglottic and tracheal stenosis can occur after extubation but TBM is uncommon. The exact mechanism is still unknown but post-intubation TBM is a life-threatening condition with high morbidity and mortality if left untreated. Early detection and timely management can improve the outcome of patients.