A 73-year-old man with a history of postpneumonectomy empyema and a long-term chest tube since 1979 presented with fever, chills, leukocytosis, and purulent fluid from the left tube thoracostomy. CT scan and bronchoscopy demonstrated a right lower lobe pneumonia and a left mainstem dehiscence with direct communication to the left tube thoracostomy. He underwent primary closure of the bronchopleural fistula with latissimus dorsi muscle flap coverage after antibiotic therapy for right lower lobe pneumonia.