Duplicated anterior urethras are a rare congenital anomaly that is exceedingly uncommon among adult patients, as surgical correction is often completed during childhood. We present the case of a 33-year-old man with uncorrected duplicated anterior urethras and urinary retention due to severe urethral stricture disease involving both of his uncorrected duplicated anterior urethras. This report highlights an operative management strategy for reconstruction to create a single, unobstructed urethra that terminates in an orthotopic meatus. Further, we provide an overview of the anatomic variants of urethral duplication.