Chronic thromboembolic pulmonary hypertension (CTEPH) is one of the indications for lung transplantation. When patients with CTEPH undergo transplantation, massive bleeding can occur because of severe pleural adhesions and collateral vessels that develop from the thoracic wall to the lungs. However, there has been no previous case report that has discussed the bleeding risk in detail. We report the case of a patient having CTEPH who underwent bilateral lung transplantation with massive blood loss (11,730 mL) in the first operation and required repeat operations for hemostasis. The patient underwent left upper lobectomy because compromised blood flew to the left upper lobe. He recovered from the operations by postoperative day 9; however, he died from pyothorax from an intractable air leak 56 days after transplantation.