Spontaneous rupture of the esophagus (Boerhaave syndrome) is a rare condition that has many possible causes, among them violent retching. The definitive treatment for the ruptured esophagus is surgical repair. Potential complications include infection in many forms, pleural effusion, and pneumothorax. This case study presents an overview of the syndrome, including morbidity, mortality, and treatment. The patient in this case is a 61-year-old man who had 1 episode of violent vomiting resulting in a perforation of the esophagus with communication into the right chest cavity. The patient underwent surgical repair of the rupture with placement of a feeding tube and creation of an esophageal diversion to promote healing of the surgical site.