We present the case of a female neonate with expiratory stridor that was caused by a bronchogenic cyst that led to tracheobronchomalacia. Rigid endoscopy revealed that a severe anterior compression of the tracheobronchial tree had caused tracheomalacia and right bronchomalacia. Computed tomography of the chest with intravenous contrast demonstrated the presence of a mediastinal mass anterior to the trachea and bronchus. Following a complete excision via a median sternotomy, histopathologic examination identified the mass as a bronchogenic cyst with respiratory epithelial lining and cartilage elements. The patient experienced a complete resolution of her respiratory symptoms postoperatively.