A 48 year-old Hispanic gentleman presented to the emergency department (ED) with 2-hour history of acute dyspnea. The patient had the history of motor vehicle accident 15 years prior to presentation. A chest x-ray done in the ED revealed pneumothorax and hydrothorax in the left chest. The patient had emergency closed tube thoracotomy with resolution of the pneumothorax. The chest tube began to drain fecal contents. A computed tomography (CT) scan of chest revealed evidence of a large diaphragmatic hernia with greater omentum and colon in chest and a colopleural fistula secondary to necrosis of incarcerated-strangulated segment of colon. The patient underwent thoracotomy with reduction of the incarcerated bowel and omentum into the abdominal cavity through the diaphragm, and the diaphragm was repaired. This procedure was immediately followed by an exploratory laparotomy with segmental resection of the transverse colon and end-to-end anastomosis. The patient did well and was discharged home after 10 days of hospitalization.