Esophageal bleeding has a broad differential. One rare cause of esophageal bleeding is an intercostal artery pseudoaneurysm, which usually presents as hemothorax secondary to trauma or an iatrogenic cause; we identified only 9 reported cases in the English literature. Rarer still is pseudoaneurysm of the intercostal-bronchial trunk, which has not been reported in the literature. We report a 61-year-old man with an intercostal-bronchial trunk pseudoaneurysm who presented with hematemesis and signs of upper gastrointestinal bleeding without previous history of trauma. This case report serves to broaden the differential for esophageal bleeding.