This case report describes a 64-year-old man with thoracic esophageal squamous cell carcinoma who successfully underwent McKeown esophagectomy despite a history of definitive chemoradiotherapy for esophageal cancer and total pharyngolaryngectomy with free jejunal graft reconstruction for hypopharyngeal cancer. The surgery required careful preservation of tracheal blood supply through limited lymph node dissection and preservation of bilateral bronchial arteries, resulting in no tracheal necrosis despite manageable postoperative complications. This is the first reported case demonstrating the feasibility of thoracoscopic McKeown esophagectomy in this complex clinical scenario.