Dysphagia is a relatively common condition in the general population and has a wide range of underlying etiologies. We present the case of a 58-year-old male who presented with a complaint of progressive difficulty swallowing for two years in duration associated with unintentional weight loss. He has been using a proton pump inhibitor therapy for more than one year, but he had only mild improvement in his symptoms. Recently, the patient started to experience neck pain during swallowing and he underwent a head and neck computed tomography scan, which demonstrated an extensive elongation of the left styloid process that measured 14.9 cm. The clinical and imaging findings were consistent with Eagle syndrome and the decision was made to perform a resection of the left styloid process. Excision of the left styloid process was made using the external cervical approach. At the follow-up visit, the patient reported a near-complete resolution of his complaints. Eagle syndrome is a very rare etiology of dysphagia. The case highlights an example of Eagle syndrome with an extremely long styloid process. This diagnosis should be considered when encountering a patient with dysphagia and neck pain.