A native of Memphis, Tennessee, Bailey enrolled in college at Southern University, where he joined other students in protest demonstrations against segregation in Baton Rouge. Consequently, he was expelled because of his involvement and finished his undergraduate studies at Clark University in Worcester, Massachusetts. Upon completing his juris doctor at Yale University in 1967, Bailey worked in New York as National Director of the Law Students Civil Rights Research Council, an organization created to assist civil rights attorneys working in the South. He then moved to the San Francisco area to practice law, and was elected to the Berkeley City Council in 1971. While he was on the City Council, Bailey's black nationalist politics was extremely controversial, resulting in his expulsion in a recall election in 1973. He returned to Memphis in 1974 and began a law practice with his brother, working as an attorney until his election to the Circuit Court of Tennessee at Memphis, where he still serves. Bailey is a founder of the National Civil Rights Museum at the Lorraine Motel in Memphis, the site where Dr. Martin Luther King, Jr. was assassinated.