Aortoesophageal fistula is rare and typically presents itself to the emergency department as Chiari’s Triad of mid-thoracic pain, sentinel arterial hemorrhage, and exsanguination after a symptom-free interval. However, fatal bleeding may be the first and last presentation of an aortoesophageal fistula. When a patient experiences massive hematemesis without witnesses, EMS may assume that bleed is of a traumatic mechanism. We present a case of a 59-year-old male with no previous medical history who was transported to a trauma center unconscious and with massive bleeding of unknown origin. Computed tomography revealed a thoracic aortic aneurysm and an aortoesophageal fistula. Bleeding was not controlled and the patient expired. Trauma bay personnel should follow an algorithm which includes a prompt tamponade of the bleed using a Sengstaken–Blakemore tube or esophageal balloon paralleled by massive transfusion and obtaining an early computed tomography scan to manage patients with massive gastroesophageal bleeding until appropriate surgical interventions can be initiated.