Boerhaave syndrome is a perforation of the esophagus caused by a sudden increase in intraluminal pressure. It is known to be associated with left-sided pleural effusion and mediastinitis, but rarely presents with bilateral effusion. Its association with the presence of a hiatal hernia is unclear. We present a patient with a hiatal hernia who developed bilateral empyemas because of Boerhaave syndrome and was treated with an endoscopically placed esophageal stent.