This case presentation involves a 57-year-old-male who suffered multiple adverse sequels from the delayed diagnosis of a large presacral mass. He initially presented with lower extremity deep vein thrombosis (DVT). Several months later, he had developed a pulmonary embolus. Imaging demonstrated a 13 × 14 cm presacral pelvic mass that occluded the right-sided venous return from the leg and caused the DVT and pulmonary embolism. An inferior vena cava filter was placed and eventually clotted. He then was referred to our institution for surgical consultation. The patient received lytic therapy and unfortunately developed hematemesis and a significant hemoglobin drop. An esophagogastroduodenoscopy (EGD) showed a black esophagus. A transthoracic echocardiogram showed a patent foramen ovale. The patient eventually stabilized and a repeat EGD a week later showed resolution of the ischemic esophagus. The patient later underwent a resection of the pelvic mass. The surgical approach and the surgical decision-making will be discussed.