Tracheal or bronchial-mediastinal fistulas are a rare entity associated to high mortality. We report a case of a 58-year-old man with an unresectable non–small cell carcinoma of the lung, treated with chemoradiation followed by bevacizumab. Approximately, 6 weeks after starting bevacizumab he developed a severe cough with copious secretions He could not lie supine due to the feeling of drowning. Investigations revealed a large tracheo-mediastinal-parenchymal-pleural fistula. Palliative management was offered with interventional bronchoscopic techniques. He was found to have a large central airway defect that obliterated almost 40% of the trachea. Under general anesthesia and positive pressure ventilation, a unique approach was used to rebuild an eroded tracheal and right main stem bronchial wall. A self-expanding metallic stent (SEMS) was placed to provide a scaffold of support, whereas a Dumon Y-stent was placed inside the SEMS. This combination allowed for a patent, stable airway; recreating the normal anatomy in a minimally invasive manner walling off the fistula. The patient was discharged 2 days after the bronchoscopic intervention, with significant palliation of his symptomatology. Eighteen months later, the upper lobe cavity persists with a stable airway and stents perfectly positioned with clinically insignificant evidence of stent related granulation in the upper trachea.