Connolly was an unsuccessful candidate for the Boston City Council in 1951, 1953, 1955, and 1957. In 1959 he won a seat on the council by finishing 9th in a race where only 8 incumbents ran for reelection. He defeated his nearest opponent, teacher and first-time candidate Thomas A. Sullivan, by less than 1,000 votes. In 1961, Connolly lost his bid for reelection, finishing 17th in the general election.
