Chondroma of the trachea is an extremely rare neoplasm. A patient is described who required surgical treatment for this abnormality on three separate occasions over a nineteen-year period. The last two instances represent either local recurrence or new primary growths. The most recent presentation was that of a very large mediastinal mass causing tracheal compression, dysphagia, and superior vena caval obstruction. The clinical and pathological features of chondromas of the tracheobronchial tree are discussed. Because of its recognized potential for local recurrence, a localized chondroma of the trachea is best managed by tracheal resection.