A 41-year-old man with a 40 pack-year history of smoking and a 6-month history of dysphagia and left otalgia presented to the emergency department with worsened symptoms. Physical examination revealed the presence of mild left ptosis, and examination of the oral cavity indicated fullness beneath the left mandible and left soft palate. Flexible fiberoptic laryngoscopy confirmed a mass in the left parapharyngeal space, with impingement on the left oropharynx to the level of the hyoid bone. A fine-needle aspirate demonstrated atypical squamous cells.