Esophageal dissection is a rare condition, characterized by disruption of the submucosa from the muscular layer of the esophageal wall. It is commonly iatrogenic in etiology and patients typically present with acute onset dysphagia, odynophagia, and retrosternal pain. The condition can be diagnosed endoscopically; however, contrast swallow studies either with CT or fluoroscopy carry less risk and are the imaging investigations of choice for this condition. Patients are managed conservatively in the majority of cases. In this case report, we present a case of chronic esophageal dissection in a 15-year-old male who had undergone endoscopic removal of a foreign body from the esophagus several years prior. We discuss the clinical features, radiological diagnosis, and management of this condition.