Penetrating aortic ulcer and intramural hematoma is one of the causes of acute aortic syndromes and can present as an emergency. It is common in older individuals with multiple risk factors and rarely presents as hemothorax on the right side. We present a young male without significant risk factors who presented acutely with the right massive hemothorax. On evaluation, he had multiple ulcers in the descending thoracic aorta, which was successfully managed with a stent graft. This case illustrates the rarity of presentation at a young age and rarity of manifestation with the right hemothorax.