The case of a 57-year-old patient is described, who presented with regional gastric cancer recurrence 1 year after a gastrectomy for a T3N1M0 (Stage IIIA) adenocarcinoma of the stomach. He underwent a radical resection with intraoperative radiation to the regional field. Two months postoperatively, massive upper gastrointestinal bleeding occurred. Operative management included a left thoracotomy, aortic cross-clamping, laparotomy, and suture repair of a fistula from the root of the celiac trunk to the gastric remnant, with a completion gastrectomy. The patient survived and underwent a delayed reconstruction and closure. Subsequently, several repeat bleeding episodes took place, from sources including the celiac, common hepatic, and proper hepatic arteries. Multiple angiographic coil embolization and surgical procedures became necessary, ultimately requiring an esophagostomy and cecostomy for intestinal diversion. A rectus abdominis flap coverage of the exposed large arteries was performed. Although two more bleeding episodes took place, the patient was ultimately managed successfully. He is currently free of disease 3 years after reexploration, able to take oral nutrition, with intermittent jejunostomy feeding supplements. The discussion highlights aspects relevant to this case: the importance of a complete regional resection during a gastric cancer resection, the management strategy for an acute catastrophic intra-abdominal bleeding, and possible mechanisms that could contribute to such bleeding, including intraoperative radiation and postoperative infection.