Chronic occlusions of the inferior vena cava (IVC) and iliofemoral veins are long-term sequelae of deep venous thrombosis (DVT) that can lead to postthrombotic syndrome (PTS). Patients may present with a wide spectrum of signs and symptoms, ranging from mild discomfort and swelling to severe venous hypertension and ulcerations. We report a 68-year-old man who had a history of left lower extremity DVT after a laminectomy and who developed PTS with nonhealing ulcers. The patient underwent a cross-pubic femorofemoral venous bypass that failed to improve his clinical status. After unsuccessful endovascular attempts for recanalization of the iliofemoral segment, a profunda femoris to IVC bypass was performed. The symptoms recurred 2 years later. Venography revealed restenosis at the caval anastomosis that did not resolve by endovascular means. A surgical revision was performed, and given the quality of the IVC, a jump bypass was created to the left renal vein. The swelling improved and the ulcers healed completely. Twenty-eight months after the complex reconstructions, he remains ulcer-free with mild edema controlled with stockings. Venous reconstructions remain a viable option for patients with symptomatic and recalcitrant nonmalignant obstruction of the large veins.