Esophageal hematoma is a disorder characterized by the sudden development of pain, hematemesis, or dysphagia, commonly with minimal precipitant. We present the case of 59-year-old man with esophageal hematoma, precipitated by eating, with massive hematemesis requiring surgical intervention. A review of 31 additional cases in the literature since 1980 is discussed. The Mallory-Weiss syndrome and Boerhaave syndrome are distinct entities with some clinical similarities.