Introduction: A 70-year-old Pakistani woman with a past medical history of coronary artery disease status post recent bare metal stent x 3 (on aspirin and clopidogrel), with a remote history (1989) of a pancreaticoduodenectomy for a benign pancreatic mass that was complicated by splenic vein thrombosis, was admitted to the hospital for worsening anemia. On admission, she was noted to have a hemoglobin of 5 g per dL (9.7 grams per dL 1 month prior). Symptoms included increased fatigue and weakness, and she reported dark stools unchanged while taking oral iron. Of note she had a history of overt, obscure upper gastrointestinal bleeding with several admissions and extensive evaluations from 2001-2012, which were unsuccessful in identifying a source of bleeding. Her most recent endoscopic studies included a normal colonoscopy and an upper endoscopy that revealed post-Whipple anatomy with a widely patent gastrojejunostomy (GJ) and small type 2 gastro-esophageal varices (GOV2) without stigmata of recent bleeding. Push-enteroscopy was performed, which identified small, nonbleeding GOV2s along the fundus. The GJ anastomosis was characterized by friable mucosa and extensive vascular ectasia. The efferent jejunal limb was normal. During the procedure, active bleeding was induced by scope trauma to the GJ anastomosis requiring patient intubation and intra-procedural transfusions. A post-procedure CT angiogram revealed prominent submucosal vasculature localized to the GJ anastomosis diagnostic of anastomotic varices with additional short gastric varices between the spleen and stomach. Moreover, the spleen was enlarged (13 cm) and the splenic vein was not visualized secondary to chronic splenic vein thrombosis. There was no evidence of cirrhosis, suggesting isolated left-sided portal hypertension. Our patient was treated with splenectomy, and has not experienced recurrent bleeding during approximately 2 years of clinical follow-up. Sinistral portal hypertension, also known as left-sided portal hypertension, is hypertension confined to the gastrosplenic side of the portal venous system. To our knowledge, this is the first case of sinistral portal hypertension leading to varices at a GJ anastomosis. Sinistral portal hypertension accounts for less than 5% of all portal hypertension, and is most commonly caused by splenic vein occlusion related to pancreatic disorders. As most patients are asymptomatic, the exact incidence is unknown, but bleeding (variceal or nonvariceal) is the most common manifestation. Splenectomy decreases venous flow through collateral vessels and decompresses associated varices. Rebleeding is rare after splenectomy in various case series.