Fungal empyema is a rare entity, particularly in immunocompetent patients. It has been noted to occur in a patient with esophageal perforation. Esophageal perforation has a wide range of clinical presentations and associated complications depending on the size and site of perforation. Although the classic presentation of esophageal perforation, also known as Boerhaave syndrome, is often dramatic with hemodynamic instability and mediastinitis. Smaller perforations and esophageopleural fistula can lead to more indolent presentation in the form of complications such as necrotizing pneumonia and pleural effusions. Here we present a 42-year-old patient with alcohol withdrawal and aspiration pneumonia, later found to have loculated pleural effusions and empyema with pleural culture growing candida and staph Epidermidis. After his mental recovery, the initiation of oral feeding led to the discovery of esophageal perforation, further complicated by esophageopleural fistula formation. He had a prolonged hospital course but remained hemodynamically stable. He was treated with an esophageal stent and feeding tube placement, as well as antifungals for candida empyema.