Background: Tracheoesophageal (TEFs) and spinal-esophageal fistulas (SEFs) are rare complications of advanced esophageal carcinoma. While TEFs are relatively well-documented, SEFs remain exceedingly uncommon and present unique neurosurgical challenges, especially when complicated by central nervous system (CNS) infections or pneumocephalus. Case Description: We report the case of a 51-year-old man with recurrent esophageal squamous cell carcinoma who developed both TEF and SEF following stent placement. The fistulas resulted in recurrent aspiration, sepsis, ventriculitis, and pneumocephalus. Radiological imaging confirmed a direct communication between the esophagus and the spinal canal, with evidence of osteomyelitis and dural breach. Despite supportive treatment, the patient succumbed to the disease. Conclusion: The co-occurrence of TEF and SEF can lead to devastating CNS complications such as ventriculitis and pneumocephalus. Early radiological recognition and multidisciplinary management are essential to mitigate neurosurgical morbidity in such complex cases.