Intramural esophageal hematoma (IEH) is a rare manifestation of esophageal wall injury with nonspecific symptoms. It may be caused by trauma or occur spontaneously. IEH is often discovered on computed tomography or esophagogastroduodenoscopy and is typically managed conservatively with supportive care to allow healing. It is frequently an isolated finding in the esophagus and seldom involves any other organ. We report a rare case of a patient discovered to have an obstructing IEH with associated hemothorax after an unrelated surgical admission.