Traumatic and iatrogenic injuries of the trachea are rare. The most common causes are motor vehicle, especially motorbike accidents. The incidence of tracheal rupture during esophagectomy is reported as 4-10 %. This complication may occur during the dissection of the upper segment of the esophagus from the posterior membranous trachea, especially when there are adhesions. We reported a tracheal rupture during esophagectomy in a 29 year old man with cancer at the post cricoid region of the trachea, which had been irradiated for three months before the operation. While the esophagus was being dissected from the trachea, a vertical rupture extending to carina occurred on the posterior wall causing severe hypoventilation. To improve ventilation the cuffed armored tubes were inserted into both main bronchi which were connected to a "Y" piece. Based on this case we discussed casualties, risk factors, symptoms and anesthetic management of tracheal rupture.