Postpneumonectomy syndrome is a rare complication of a pneumonectomy. Patients may experience dyspnea, stridor, recurrent pulmonary infections, or dysphagia due to rotation and shift of the mediastinum. The current intervention of choice involves the placement of a tissue expander in the empty hemithorax to realign the mediastinum. Because this treatment can present with intraoperative anesthetic challenges and requires close monitoring, we present this case to highlight specific concerns that may need to be addressed including difficulties ventilating, complete airway collapse, hemodynamic instability, and pain control perioperatively.