The elective surgical airway is the definitive management for a tracheal stenotic lesion that is not a candidate for tracheal resection, or who has failed multiple-tracheal dilations. This case report details the management of a patient who has failed an elective awake tracheostomy secondary to the inability to be intubated as well as severe scar tissue at the surgical site. A combination of regional anesthesia and venovenous bypass is used to facilitate the surgical airway management of this patient. Cerebral oximetry and a multidisciplinary team approach aid in early detection of an oxygenation issue, as well as the emergent intervention that preserved this patient's life.