Chondrosarcomas are rare malignant tumors of mesenchymal origin. First described in 1816, laryngeal chondrosarcomas are rare tumors of the head and neck.1 Laryngeal chondrosarcomas account for <0.2% of head and neck malignancies and ∼1% of laryngeal neoplasms.2 Due to their infrequent occurrence, treatment strategies are not well defined and borrow principles of management from sarcomas arising in more commonly affected areas of the body.3 While conservative surgery is the primary treatment, laryngeal preservation does not supersede the application of sound oncologic principles.4 A 55 year old male with a history of alcohol and tobacco use, gout, diabetes mellitus and hypertension presented with hoarseness. Upon further evaluation, he was diagnosed with a low grade chondrosarcoma of the right cricoid cartilage. The patient was subsequently taken for a laryngofissure to excise the lesion with a posterior cricoid split and rib graft interposition to reconstruct the larynx. The patient was later decannulated, tolerating an oral diet and did well for several years. However, he represented with dyspnea and was found to have an obstructing right posterior cricoid lesion on imaging and laryngoscopy. Biopsy confirmed the lesion to be a spindle cell sarcoma. After an extensive discussion of treatment options, the patient was taken for a total laryngectomy. On postoperative day number two, the patient spiked a fever. Subsequent CXR revealed a pneumonia and he was treated with intravenous antibiotics. On postoperative day number five, he experienced a flare of his gout which prompted a rheumatology consult and bilateral knee aspirations. On postoperative day number seven, a barium swallow study revealed a minimal right posterior pharyngeal leak. The patient was subsequently discharged home on enteral feedings via a nasogastric tube. At two months follow-up, the patient was tolerating an oral diet and is awaiting the start of radiation therapy.