A 55-year-old man presented to the emergency department with a chief complaint of right-sided chest pain and was found to be severely anemic, requiring multiple blood transfusions. The patient's history was notable for a Billroth II procedure performed 22 years earlier for peptic ulcer disease. The patient was admitted to rule out myocardial infarction and for work-up for severe anemia. The stool specimen was guiac positive, and subsequent upper and lower endoscopy revealed a large, tannish-red polypoid mass arising from the gastrojejunal anastomosis created with the prior Billroth II procedure. No symptoms of bowel obstruction were present. Multiple endoscopic biopsies were performed, all of which were negative for malignancy.