Tracheo-esophageal fistula is a well-described congenital abnormality treated surgically upon diagnosis. Although respiratory-related and reflux-related complications are frequent, recurrent fistula and diverticulum can occur. This case report describes the rare occurrence of a gross type B fistula repaired at birth, which was then asymptomatic for nearly 30 years until presentation with chest pain. Upon workup, the patient was found to have an isolated tracheal diverticulum without recurrent fistula. We highlight the need for a focused workup despite the length of time since fistula repair and the varied treatment modalities described in the literature.