Aortogastric fistulas are a rare but usually fatal entity that presents as an acute gastrointestinal bleeding. The authors present the case of a 65-year-old man who had undergone a Nissen fundoplication and presented in the emergency room with syncope secondary to massive upper gastrointestinal tract bleed. Despite aggressive resuscitation and prompt operative intervention with repair of the gastric ulcer and closure of the aortic side of the fistula, he succumbed to the complications of hypovolemic shock. Overview of the pertinent literature with discussion of the most common causes of aortogastric fistulas as well as guidelines for intraoperative management are also presented.