We present the case of a 49-year-old man with right upper lobe adenocarcinoma invading the right brachiocephalic vein and the origin of the superior vena cava. En bloc resection of right upper lobe with the involved venous segments was carried out through a median sternotomy. Venous pathway was reestablished with a Gore-Tex (W.L. Gore & Assoc, Flagstaff, AZ) prosthesis. Postoperative course was marked by right pneumonia complicated by empyema. The patient underwent thoracotomy with completion pneumonectomy and latissimus dorsi transposition to cover both the prosthesis and the bronchial stump, as well as to fill the cavity. A favorable outcome was observed and long-term survival achieved.