Small bowel diverticulosis is rare with an incidence of 1-2% in the general population. It is an uncommon cause of gastrointestinal bleeding that ranges from obscure to overt bleeding. Large ileal diverticula are extremely rare and bleeding complications can result in high overall mortality. A young gentleman presented with persistent per-rectal bleeding and drop in hemoglobin level. He was recently diagnosed with acute myeloid leukemia and was undergoing chemotherapy. A computed tomography scan of the abdomen and pelvis revealed a giant ileal diverticulum. In view of on-going bleeding, he underwent double balloon enteroscopy which revealed active bleeding from an ulcer within the giant ileal diverticulum and successful hemostasis was performed with hemostatic clips. Small bowel diverticulosis though uncommon has to be considered during workup for gastrointestinal bleeding. Endoscopic treatment is a modern approach towards small bowel diverticular bleeding that is effective and less invasive.