Chest pain in low risk patients is a common ED presentation. Rarely, these patients can have life-threatening conditions requiring timely diagnosis and intervention. There are currently standardized protocols for diagnosing cardiac ischemia, pulmonary embolus, and aortic dissection in low risk patients. Even more rare entities such as esophageal perforation, hemo/pneumothorax, and cardiac tamponade must also be kept in mind. We present the case of chest pain in a 33 year old male reporting no significant past medical history who developed spontaneous massive hemothorax while being evaluated in the ED. Subsequent investigation revealed that the patient had neurofibromatosis; the etiology of aneurysmal rupture in neurofibromatosis is discussed.