GIST tumors are unusual in the young and middle-aged and a high index of suspicion is needed for its possible diagnosis in young patients who present with upper gastrointestinal bleeding. Appropriate imaging such as a computed tomographic scan (CT scan) may identify this tumor that may easily be misdiagnosed as a bleeding peptic ulcer disease. We present a case of a healthy 38-year-old man with no alcohol use who presented with epigastric pain and melena and subsequent torrential bleeding uncontrolled during endoscopy necessitating an emergency exploratory laparotomy by the general surgery team. The bleeding intraluminal component of the tumor with gross splenic and pancreatic involvement was identified and surgical management consisted of a wedge resection of the greater curvature of the stomach incorporating the tumor and the spleen with successful dissection of the tumor off the tail of the pancreas. Histology was positive for C-KIT and DOG-1 markers. The postoperative course was uneventful, and he is presently on Imatinib mesylate.