We report a case of a 46-year-old Malay woman with underlying hypothyroidism post thyroidectomy who presented with worsening breathlessness, orthopnoea, productive cough and left-sided pleuritic chest pain of 3 days duration. Chest X-ray on admission showed left-sided massive hydropneumothorax. Pleural tapping revealed empyema. A chest tube was inserted immediately. The culture of pleural fluid grew Streptococcus constellatus The patient was treated with antibiotics for a total of 6 weeks and underwent open thoracotomy and decortication during admission. Subsequently, her lung condition improved and there was no evidence of recurrence during follow-up.