Boerhaaves syndrome rarely presents as massive hemothorax with hypovolemic shock. We report the case of a 28- year-old male with sudden onset chest pain and dyspnea occurring after lunch. After chest roentgenography showed pneumothorax with effusion in the left pleural cavity, a chest tube was inserted and more than 2000 mL bloody effusion was drained in one hour. After transfer to our hospital, emergent video-assisted thoracic surgery was done. Considerable food- containing material was found in the left thoracic cavity. A longitudinal rupture, approximately 6 cm in length, was located at the left posterior-lateral wall of the lower third of the esophagus: A bleeder in the muscle layer was noted. Primary esophageal repair and a subsequent feeding jejunostomy were done. The patient was discharged two weeks after surgery. There was no dysphagia at six months’ follow-up.