Upon leaving the army, Wilkinson began law school at the University of Virginia School of Law in Charlottesville. In 1970, after completing only one year, Wilkinson took a leave of absence to run (at age 25) for a Virginia seat in the United States House of Representatives. He ran as a Republican against 3-term incumbent Democrat David E. Satterfield III and later joked about losing by a significant margin, noting that Satterfield had a billboard urging voters to send Wilkinson back to law school. Wilkinson then resumed his legal studies and graduated with a Juris Doctor in 1972 (when Satterfield faced no opposition) and soon passed the Virginia bar exam.