Tracheomediastinal fistula (TMF) is an uncommon condition and carries a high mortality. We report the anesthetic management of a patient with TMF using stent insertion via rigid bronchoscopy. The TMF was a complication of double-lumen endotracheal tube insertion resulting in a tension pneumomediastinum. Initial intraoperative attempts to ventilate the lungs and overcome the air leak with high gas flow of 45 L/min via the side port of the bronchoscope resulted in a pneumothorax. This case report demonstrates that high-frequency jet ventilation can minimize the air leak and avoid barotrauma during anesthesia for TMF repair.