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Metastatic esophageal adenocarcinoma to the urinary bladder is extremely rare and aggressive. We discuss here the case of an 83-year-old male with history of esophageal adenocarcinoma treated with chemoradiation therapy and esophagectomy who presented with gross hematuria and lower urinary tract symptoms. Pathology of the bladder tumor after transurethral resection demonstrated invasive adenocarcinoma of both the bladder and the prostatic urethra consistent with metastatic esophageal adenocarcinoma.