Cummings began his career as a farmer. He was the owner of a grocery store, and he became a lawyer.[2] He served as a member of the Tennessee Senate in 1927 and 1937.[2]
Cummings was elected as the mayor of Nashville in 1938. He was reelected in 1939, 1943 and 1947.[1]
In 1939, Cummings appointed black banker James Carroll Napier to the Nashville Housing Authority.[3][4] In 1940, he sent a police honor guard to Napier's funeral.[5] In May 1948, he announced the hiring of seven black policemen to join the Nashville police force.[6] He hastened to add they would only work in black neighborhoods, arguing they would be more qualified to keep the order in black neighborhoods.[6] They shared only one patrol car and weren't allowed to arrest white Nashvillians.[6]