Trans-mediastinal herniation of a lung bullae is an extremely rare condition. Here we present a case of a 75-year-old patient with a clinical history of chronic obstructive pulmonary disease and emphysema presenting with a right contralateral pneumothorax secondary to a trans-mediastinal herniated lung bullae. Herniation occurred through a mediastinal pleural defect; we call this event a paradoxical pneumothorax. To our knowledge this is the first report in the medical literature. The patient was successfully treated using a VATS approach with a right pleurodesis, a left thoracoscopic trans-mediastinal hernia reduction and bullectomy.