[4] Although Virginia's Byrd Organization (while also Democrats) opposed many of President Franklin Delano Rooosevelt's reforms, and especially President Harry S Truman after he abolished racial segregation in the armed forces, Whitehead served as one of the Democratic Electors for FDR's third term in 1936, and later as Virginia State Chairman of the Truman Barkley Straight Ticket Committee in 1948.
He was also a director of The First National Bank of Nelson County, and active in the Ruritan club, the American Legion, and on the Executive Committee of the Virginia State Bar.
A Democratic member of the House of Delegates from 1942-1960, Whitehead often opposed the Byrd Organization, which gave him poor committee assignments and often sought to marginalize him.
[5] He vehemently opposed radical interpositionists led by James J. Kilpatrick, and thought U.S. Rep. Howard Smith (a Byrd organization lieutenant) was a moderating voice, so one analyst called him a "cushioning segregationist.
"[6] The most ardent segregationists proposed to withhold all state funds or even close any school or district that integrated, a stance Whitehead vehemently opposed.
[8] After a three-judge federal panel and the Virginia Supreme Court on January 18, 1959 declared key aspects of the Stanley Plan unconstitutional, Whitehead was appointed to the Perrow Commission, which sought gradual integration.