The lung tumors with carinal involvement are frequently managed with tracheal sleeve pneumonectomy and tracheobronchial anastomosis without use of cardiopulmonary bypass (CPB). Various modes of ventilation have been described during tracheal resection and anastomosis. Use of CPB during this period allows the procedure to be conducted in a more controlled way. We performed tracheal sleeve pneumonectomy for adenoid cystic carcinoma of left lung involving carina. The surgery was performed in two stages. In the first stage, left pneumonectomy was performed and in the second stage after 48 h, tracheobronchial resection and anastomosis was performed under CPB. Second stage was delayed to avoid excessive bleeding (due to heparinization) from the extensive vascular raw area left after pneumonectomy. Meticulous peri-operative planning and optimal post-operative care helped in successful management of a complex case, which is associated with high morbidity and mortality.