We experienced failed airway management in a patient who had partial mandibulectomy and reconstruction with free-flap. 40 year-old man (height: 164 cm, body weight: 59 kg) with malignant melanoma on #38 tooth area of mandibular body was scheduled for partial mandibulectomy and reconstruction with free flap. Approximately fifteen-hours after surgery, the patient was extubated without complication. Seven hours after extubation, we experienced respiratory failure andfailed airway managementdue to airway edema and neck. We failed orotracheal intubation with direct laryngoscopy andlaryngeal mask airway, thus we tried tracheostomy but the patient was hypoxic state for more than 30 minutes. The patient had got hypoxic brain damage in whole cerebral cortex and basal ganglia. We should have the policy of airway management of the patients who have massive oro-maxillo-facial surgery and all medical personnel who treat these patients should be educated the policy and airway management methods.