This report documents a unique case of syphilis with esophageal involvement. Such a presentation is exceedingly rare in the modern era, particularly among patients without human immunodeficiency virus. Most instances were documented in the 1900s and earlier. Our patient presented with months of odynophagia and recurrent oral lesions. He was found to have a sizeable esophageal ulcer on endoscopy, with biopsy confirming the diagnosis of syphilis. His symptoms quickly resolved with intramuscular penicillin. This case highlights the importance of keeping a broad differential for odynophagia and suspicious lesions, cutaneous or mucosal.
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