Background: Esophageal cancer is the 8th most common and 6th most deadly malignancy worldwide. It is an aggressive type of cancer with poor prognosis, despite advances in therapeutic methods including those in thoracoabdominal surgery, chemotherapy and radiotherapy. It rarely manifests in young patients, but occurs frequently in older people. It has been related with achalasia regarding mainly the squamous cell carcinoma rather than the adenocarcinoma. Infiltrating esophageal tumors and radiotherapy can lead to the development of aortoesophageal fistula, a pathological communication between the aorta and the esophagus. Case: We present the case of a 24-year-old male patient with a known history of achalasia for almost 15 years with a history of heavy smoking and drinking that presented with advanced lower esophageal adenocarcinoma. The patient was submitted, as per to his will, directly to Ivor Lewis esophagogastrectomy. One month later, dysphagia was manifested due to stenosis of the anastomosis, without any signs of local recurrence, and an esophageal metallic stent was placed. In the 3rd postoperative month, upper gastrointestinal bleeding presented due to an aortoesophageal fistula, caused by anastomotic dehiscence due to local recurrence and pressure from the stent, which was treated surgically. The patient, refusing chemotherapy at all stages, developed peritoneal carcinomatosis and died 6 months after surgery. Conclusion: Esophageal cancer is an aggressive type of cancer with a poor prognosis that is typically diagnosed in advanced stages. Despite the development of new therapeutic approaches, the high recurrence rate and the poor prognosis remain.