Urgent airway management is challenging because time constraints limit thorough evaluation and planning before endotracheal intubation. In this report, we describe a case in which an airway history review revealed extraordinarily complex airway anatomy that led to a decision not to attempt intubation in a man with end-stage chronic obstructive pulmonary disease. We emphasize the utility of reviewing history and imaging before attempted urgent intubation. We discuss the importance of a multidisciplinary approach that includes the patient, their family, and consultants when high-risk intubation is contemplated. The ethical role of the anesthesiologist is also discussed.