A native of Memphis, Tennessee, Bailey pursued higher education at Southern University, where he actively participated in student protests against segregation in Baton Rouge, ultimately leading to his expulsion from the institution. Undeterred, Bailey transferred to Clark University in Worcester, Massachusetts, where he completed his undergraduate studies.
Following the completion of his juris doctor at Yale University in 1967, Bailey relocated to New York, where he served as the National Director of the Law Students Civil Rights Research Council, an organization established to provide support to civil rights attorneys working in the South.
Subsequently, Bailey moved to the San Francisco area to practice law and was subsequently elected to the Berkeley City Council in 1971. However, his black nationalist politics sparked intense controversy, ultimately resulting in his expulsion from the City Council in a recall election held in 1973.
Returning to Memphis in 1974, Bailey established a law practice with his brother, working as an attorney until his election to the Circuit Court of Tennessee at Memphis, where he continues to serve to this day.
In addition to his distinguished legal career, Bailey is also a co-founder of the National Civil Rights Museum at the Lorraine Motel in Memphis, the site where Dr. Martin Luther King, Jr. was assassinated.