After admission to the Alabama bar, Boutwell practiced law in Birmingham, for many years, first with Sam Pointer during the Great Depression, then with Burgin Hawkins, as Bouthwell, Pointer & Hawkins. He was also active in the Birmingham Junior Chamber of Commerce. He was also active in his Methodist Church, as well as the Elk, and Mason fraternal organizations. Beginning in 1939, Boutwell was elected to the state Democratic Committee, representing District 9. In 1944, he was one of Alabama's representatives at the National Democratic Convention. He also twice served as chair of his state party's finance committee. Boutwell first won election in 1946, as Birmingham voters elected him to the Alabama Senate. After he won re-election in 1950, fellow senators elected Boutwell as their president pro-tem. During his third four-year term, Boutwell served as Chairman of the Interim Legislative Committee on Segregation in the Public Schools, and in response to the U.S. Supreme Court desegregation decisions in Brown v. Board of Education, secured passage of a pupil placement act designed to maintain segregation. He won statewide office, as lieutenant governor, in 1958. Considered a moderate by many in Birmingham early in the Civil Rights Movement, Boutwell's election to the City Commission on April 2, 1963 was seen as a rejection of vehement segregationist Eugene "Bull" Connor. Connor attributed his loss by 7,982 votes to a 10,000-strong “Negro bloc vote”; and in fact Fred Shuttlesworth had delayed mass demonstrations of the "Birmingham Campaign" until after the election. Dr. Martin Luther King, Jr.'s famous "Letter from Birmingham jail" was addressed to Boutwell; King had been arrested on Good Friday after Boutwell had vowed to arrest, jail and punish anyone who disturbed the public peace and safety. Lame duck Connor in fact met those demonstrations with police dogs and fire hoses, and the movement's leaders and Birmingham businessmen declared a truce on May 10. Later than year, Boutwell declared that school integration was not in children's interest. He was in office a few months before the forced integration of Birmingham schools by the National Guard and the bombing of 16th Street Baptist Church, which killed four young girls. Boutwell was defeated for re-election in 1967. His pupil placement act and its popular freedom of choice provision were declared unconstitutional by federal courts in 1967.
Personal life
In 1934, Boutwell married Helen Balfour. They had a daughter and two sons
