In 1966, Rawlings first ran for federal office, challenging Congressman Howard W. Smith, a powerful eighteen-term incumbent and Byrd Organization stalwart who had been in office since the Hoover administration, in the Democratic primary. As chairman of the House Rules Committee as well as a segregationist, Smith had used his position for years to block civil rights legislation. Rawlings, drawing on the support of black voters who had only recently been enfranchised by the Civil Rights Act of 1964, defeated Smith by a vote of 27,115 to 26,470, a margin of just 645 votes. The Fredericksburg Free Lance-Star declared his victory "the upset of the century." In the general election, however, Rawlings lost to Republican nominee William L. Scott, who received the support of most of Smith's primary voters, by a vote of 50,782 to 37,929, a nearly 15% margin. In 1970, Rawlings, now retired from the House of Delegates, sought the Democratic nomination for the United States Senate, challenging Senator Harry F. Byrd Jr., the son of the Byrd Organization's late founder and boss. After the Democratic defeats in the 1969 general election, the younger Byrd changed his party affiliation from Democratic to independent and refused to sign a loyalty oath that pledged him to support all Democratic nominees for office. In that Democratic primary, Rawlings narrowly placed first with 58,874 votes over fellow liberal State Senator Clive L. DuVal II, who collected 58,174 votes. Although DuVal was entitled to ask for a runoff, he declined to do so, and Rawlings became the Democratic nominee. In the general election, however, Rawlings secured only 294,582 votes, compared to 506,237 votes for Senator Byrd. Republican Ray L. Garland placed third with 144,765 votes.
Later life
Rawlings then returned to his law practice, but did not leave politics entirely. In 1972, he joined his friend and ally Henry Howell, a former Democratic State Senator who had been elected as Lieutenant Governor as an independent in a 1971 special election, as well as supporters of Democratic presidential candidateGeorge McGovern, to attempt to purge the official machinery of the Democratic Party of the last vestiges of the Byrd Organization. As a result of these activities, Rawlings was elected as a member of the Democratic National Committee and as chairman of the Eighth District Democratic Committee. The next year, Howell ran for Governor of Virginia as an independent without a Democratic opponent and with the support of the party organization. In 1975, Rawlings and his wife, Rosalie, divorced after Rawlings came out to her as gay. After moving to Fairfax County with his new partner, he continued to practice law. In 2000, he was caught embezzling from a client's account. He pleaded guilty and received a suspended sentence of five years. He died of natural causes on April 22, 2009 at Mary Washington Hospital in Fredericksburg.
