The development of a gastrocardiac fistula is a rare complication following retrosternal gastric conduit creation. We report a case of a 64-year-old male who presented three years after esophagectomy with massive hematemesis. A fistulous connection between his gastric conduit and right ventricle was identified and successfully treated. Although the patient had an atypical presentation and lacked most of the commonly cited risk factors, the combination of peptic ulcer disease and Candida overgrowth resulted in the formation of a gastrocardiac fistula. Adherence to treatment principles including prompt surgical intervention, adequate coverage of the repair, and antimicrobial therapy against Candida species provides the highest likelihood of success in addressing this potentially lethal disease process.