A 73-year-old man with history of metastatic esophageal cancer and esophageal stent placement 4 months prior presentation presented after a syncopal episode related to severe cough. On arrival to the emergency department he was unresponsive, hypoxemic and acidotic. The patient was orotracheally intubated. Computed tomography of chest revealed extensive consolidation involving the right lung. Significant air leak with returning was noted post intubation with tidal volumes that were less than 50% of the initial volume. The endotracheal tube was replaced with defected cuff noted. The leak persisted and an emergency bronchoscopy revealed two large openings around secondary carina consistent with bronchial tears related to bronchoesophageal fistulization. These wall abnormalities appeared to enlarge with each delivered tidal volume. The air was escaping through the stomach and through the mouth. A flat film of the abdomen revealed large amounts of gas in stomach and bowel. The ET tube was pulled back and left main stem intubation was done under bronchoscopic guidance. The patient’s oxygen saturation improved and the leak resolved.