Long-term silicone stents in the airway present challenges for removal without rigid bronchoscopy. Here, we present a case of a 46-year-old female with a tracheoesophageal fistula and a silicone stent placed 15 years ago following surgical repair after difficult intubation during hysterectomy. Due to tracheal position, rigid intubation was unsuccessful, necessitating extended stent placement. Recently, the patient reported dyspnea and wheezing, and bronchoscopy revealed distal stenosis near the stent. In our clinic, flexible bronchoscopy and balloon dilation were performed, and initial attempts at stent removal using foreign body forceps failed due to fragmentation. We successfully removed the stent using an endotracheal tube cuff, a technique that, to our knowledge, has not been previously described. Post-removal cryotherapy treated granulation tissue, with follow-up bronchoscopy showing significant improvement. This case, the longest silicone stent follow-up reported, highlights an effective alternative removal technique, avoiding high-risk surgery and contributing to airway management practices.