After service in the United States Army Air Forces in World War II, he resumed legal studies at Richmond, obtaining a JD degree in 1947.

[1] In 1957, midway through his second term, he won election to the House of Delegates, a part-time position which enabled him to have a private legal practice, although he could no longer hold the prosecutorial job.

[5] Philpott and another freshman, Robert L. Clark, both Democrats and members of the Byrd Organization, represented the two-member district consisting of Henry and adjoining Patrick Counties, as well as the city of Martinsville.

[6][7][8][9] This election took place during the period of massive resistance to racial desegregation in Virginia, led by United States Senator Harry F. Byrd.

Philpott blocked a 1982 bill by Senator Douglas Wilder of Richmond to create a state holiday to honor the birthday of Martin Luther King Jr. Later that year, he publicly referred to five African-American legislators as "boys", a statement for which he apologized the next day.