Tracheobronchomalacia is a weakness of the trachea and bronchi due to abnormal cartilage and muscular support leading to airway obstruction. We report a case of an adult former smoker without pulmonary symptoms who underwent robotic-assisted laparoscopic cystectomy in the steep Trendelenburg position. After repeated episodes of hypoxemia, bronchoscopic examination revealed collapse of the distal trachea and bronchi, supporting a diagnosis of tracheobronchomalacia. Tracheomalacia is an underdiagnosed condition in patients with a smoking history and may mimic other obstructive diseases. The anesthesiologist should remain vigilant to the possibility of airway collapse in former smokers, specifically in cases of increased intrathoracic pressure.