We present a 76-year old man with a two year history of Gleason 9 prostate cancer (PCa) presenting with penile pain, erythema, and a fungating mass on the glans. Imaging at initial PCa diagnosis revealed confined disease. His prostate cancer was previously treated with radiation and androgen deprivation therapy (ADT) with initial laboratory response via prostate specific antigen (PSA) levels, however his PSA began to rise six months following cessation of ADT. Shared decision making resulted in partial penectomy for symptomatic management. Computed tomography (CT) and bone scan performed after surgery were not definitive for metastatic disease.