Small bowel obstruction secondary to primary cancer, such as carcinoid and adenocarcinoma, is not unusual. Less frequently, hematological metastasis from breast, lung, and melanoma can occur. However, metastasis from urothelial bladder carcinoma is extremely rare. In this index case, we describe a 71-year-old Caucasian man with a prior history of urothelial bladder carcinoma. He was treated successfully with chemoradiation and local resection a year prior to his current presentation with small bowel obstruction which required surgical resection of a loop of jejunum, which was found to be caused by obstructive, metastatic urothelial bladder carcinoma on pathology. Therefore, one should consider the possibility of secondary obstructive malignant lesions arising from the urinary bladder in such a patient when presented with bowel obstruction and a history of urothelial bladder carcinoma.