Considered a moderate by many in Birmingham early in the civil rights movement, Boutwell was elected to the City Commission on April 2, 1963; he was selected as President of the Commission, equivalent to mayor under that system. His election 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. Martin Luther King Jr.'s April 1963 "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 that year, Boutwell declared that school integration was not in children's interest. He was in office for the forced integration of Birmingham schools by the National Guard and the bombing of 16th Street Baptist Church, which killed four young girls.