He served in the U.S. Army's 11th Airborne Division in the Pacific Theater in World War II, and was active in the Freemasons.
Senator Harry F. Byrd refused to allow desegregation of Virginia's schools after the U.S. Supreme Court's decision in Brown v. Board of Education.
Thus, Webb's was one of the few moderate voices during the special legislative session that ultimately adopted the Stanley Plan, portions of which were declared unconstitutional by both the Virginia Supreme Court and a three judge federal panel on January 19, 1959.
[2] Hirst declined to seek reelection, and after a multi-candidate Democratic primary Dorothy S. McDiarmid, who ran against the Byrd Organization's school closing strategy and was elected (and Webb was re-elected) in November, 1959.
Nearly a decade after his first electoral win, Webb (together with Stone and Senators C. Harrison Mann and John A. K. Donovan) became named plaintiffs in the reapportionment case ultimately decided (in Northern Virginia's favor) by the U.S. Supreme Court in Davis v. Mann.