We report the case of a 52-year-old patient with type 2 diabetes mellitus diagnosed with adenocarcinoma rectum, presenting with the complaint of breathlessness to the emergency department. Chest radiograph done showed a left-sided hydropneumothorax with mediastinal shift to the right side. Tube thoracostomy was done. Pleural fluid was exudative; there was no evidence of malignancy. The patient developed a right-sided pleural effusion; anaerobic bacteria were grown on pleural fluid culture. Computed tomography (CT) of the chest was done in view of the new onset empyema on the right side. The CT showed pneumomediastinum and periesophageal air pockets. Orally administered methylene blue had appeared in the pleural drain confirming the diagnosis. The patient was taken up for feeding jejunostomy and repair of tear was planned for a later date. He succumbed to sepsis due to empyema.