This is a rare presentation of a morbidly obese male with a massive retropharyngeal goiter causing laryngeal compressive symptoms and unique airway management challenges. Flexible laryngoscopy revealed a retropharyngeal mass circumferentially compressing the oropharynx and supraglottis and preventing the visualization of the glottis. Awake tracheostomy was performed before total thyroidectomy. Airway compression from a goiter typically results from substernal extension, which usually does not cause difficulty with endotracheal intubation. Extensive retropharyngeal extension can cause supraglottic obstruction of the airway. In these cases, optimal management consists of a closely coordinated approach between anesthesia and surgery teams to establish a surgical airway.