We report a case of an 80-year-old female with two prior thoracotomies for benign solitary fibrous tumor of the pleura (SFTP) presenting with a two-month history of shortness of breath. Computed tomography revealed a pleural-based recurrence and operative excision revealed multiple adherent tumors throughout the thoracic cavity. Pathologic examination demonstrated malignant degeneration of this previously benign tumor. We consider the importance of recurrence of benign SFTP and the significance of surgical care and follow up of patients with this rare tumor.