Cleary was appointed a Liverpool Justice of the Peace in 1927. A member of the Labour Party, he contested the 1929 East Toxteth by-election and fought the seat again at the general election later that year, performing creditably in a safe Conservative seat. In the 1931 general election Cleary fought the West Derby division of Liverpool. This was a terrible year for Labour and his Conservative opponent trounced him by over 23,000 votes. He was the councillor for Garston ward from 1927 to 1941.