Boerhaave syndrome is a rare entity which classically presents with perforation and mediastinal sepsis. The patients' outcome is directly related to the length of time required to diagnose and surgically address the syndrome. Atypical presentations can contribute to a delay in recognizing the phenomenon, which portends poorly. The case of a man with postemetic esophageal perforation presenting with a massive left hemothorax is presented. To the authors' knowledge, this is the only case of this type to be described in the literature.