In his first bid for City Council in 1939 in Los Angeles City Council District 1, representing the San Fernando Valley, McCloskey survived the first round of voting but was defeated by the incumbent, Jim Wilson, in the final election. In the 1941 final, though, it was McCloskey who was the winner over Wilson. McCloskey had no serious opposition in 1943 and was reelected in the primary vote. In 1945, however, he was ousted by Leland S. Warburton in the final election.