Winstead was elected as a
Democrat to the
Seventy-eighth and to the ten succeeding Congresses (January 3, 1943 – January 3, 1965). Like nearly all other Mississippi Democrats, he was an ardent
segregationist and signed the
Southern Manifesto after the United States Supreme Court ruled in
Brown v. Board of Education (1954) that segregated schools were unconstitutional. Having won the Democratic Party primary in what was essentially a one-party state since the state constitution's effective
disfranchisement of blacks in 1890, Winstead was unopposed in his first bid for Congress. With its backing at that time almost entirely African-American, the
Republican Party had become comatose after disfranchisement of almost all of its base and most of its membership. Democratic nomination subsequently became
tantamount to election, thus, Winstead faced an opponent once during his ten successful campaigns. However, in 1964, Winstead was defeated by
Republican challenger
Prentiss Walker by a shocking 11-point margin. Winstead was swept out in large part from the district
and state swinging dramatically to support
Barry Goldwater's presidential bid. Goldwater carried over half of Mississippi's counties by over 90 percent of the vote. ==Return to private life==