Urethral cancer after urethral reconstruction is an under-recognized, uncommon disease associated with significant morbidity and mortality. The survival rates of patients with carcinoma of the bulbar urethra are as low as 20%-30%. Stricture recurrence and unrecognized malignant changes present prior to reconstruction are major risk factors for urethral cancer. Skin substitution urethroplasty is subjected to higher rates of recurrence, which lends to the potential for carcinogenesis. We present a case of a 59-year-old male who underwent multi-stage skin substitution urethroplasty who developed urethral carcinoma 20 years later.