CASE PRESENTATION: 65 yo male with a history of hepatitis C, alcoholism and prior small bowel obstruction (SBO) related to abdominal surgery was admitted to our hospital following 3 days of abdominal pain and emesis attributed to a partial SBO. The admission chest film (CXR) was unremarkable except for minor basilar atelectasis. On hospital day 2, he developed acute chest pain with ischemic EKG changes. Cardiac cath revealed no evidence of obstructive coronary artery disease. Post procedure, he developed excruciating chest pain radiating to his back associated with tachycardia, hypotension and absent breath sounds over the left lung. CXR demonstrated interval opacification of the left hemithorax with mediastinal shift. An emergent needle thoracostomy produced air and dark fluid containing food debris, followed by tube thoracostomy which drained 4 liters of bilious, enteric output. Chest CT demonstrated a large left hydropneumothorax with free air around the esophagus. EGD demonstrated a circumferential area of “black esophagus” in the distal third of the esophagus consistent with necrosis and perforation. The patient underwent emergent esophagectomy with cervical esophagostomy, diagnostic laparotomy, and gastrostomy tube placement. His post-operative course was complicated by hypoxemic respiratory failure, ischemic stroke, and gastrointestinal hemorrhage on hospital day 21 leading to cardiac arrest and death.