Prostate cancer is the most common noncutaneous malignancy in American men. Its lymphatic drainage is very well established throughout literature. We report the case of a 72-year-old Caucasian male with elevated serum prostate-specific antigen and biopsy-confirmed high-risk prostate cancer who underwent multiparametric magnetic resonance imaging (MRI) for staging and treatment planning. The imaging revealed suspicious lymph nodes in the left ischiorectal and right obturator fossae that were biopsy confirmed as metastatic prostate adenocarcinoma. Herein, we present the divergence from the well-established lymphatic drainage of prostate cancer and the role of MRI in detecting this prostate cancer site of spread.