Gastrointestinal stromal tumor (GIST) is the commonest gastrointestinal mesenchymal tumor, which rarely metastasizes to lymph nodes. Therefore, unlike cases of adenocarcinoma, lymphadenectomy is seldom warranted. We describe an unusual case of a polypoid GIST of the small bowel which metastasized to the regional mesenteric lymph nodes at the time of primary surgery. The patient was a 79-year-old female who presented with partial bowel obstruction and anemia. The presented case has three unusual features, as the tumor was grossly pedunculated, microscopically pleomorphic, and featured mesenteric lymph node metastasis at the time of diagnosis.