Born in Crystal Springs in Copiah County outside Jackson, Mississippi, Bailey attended the University of Mississippi at Oxford, where in 1879 he joined the prestigious Delta Psi fraternity. Bailey was admitted to the bar in Mississippi in 1883. He moved to Gainesville in north Texas in 1885, where he continued to practice law. He had been politically active as a Democrat in both Mississippi and his new home and had a reputation as an excellent public speaker who promoted Jeffersonian democracy. He was elected to the House in 1891 and quickly distinguished himself as leading advocate for free silver, which contributed to his election as Minority leader of the United States House of Representatives in 1897. He exerted considerable influence on his colleagues, but also struggled to unify his divided caucus. On April 14, 1897, some House Democrats, led by David A. De Armond sought to block a three day adjournment, a maneuver understood as a repudiation of Bailey's cooperative relationship with Republican Speaker Thomas Brackett Reed. Bailey's most severe disappointment as minority leader came in 1898, when Bailey argued that congressmen who had accepted commissions to serve in the army without resigning from Congress had violated the Ineligibility Clause of the Constitution. Despite Bailey's advocacy, when the House voted on a motion for whether to consider a resolution which would have removed several members from Congress who had simultaneously held commissions during the Spanish-American War, a majority of Democrats opposed the motion. The next day, Bailey declared that he would not be a candidate for minority leader in the next Congress. He was elected to the U.S. Senate in 1901. His political career was tarnished by an assault against Senator Albert J. Beveridge, an Indiana Republican. Subsequent investigations brought to light suspicious income and financial ties that Bailey had to the burgeoning oil industry. Nevertheless, financial allegations against Bailey in 1906 threatened his reelection to the Senate, a task then the prerogative of the Texas legislature, rather than party voters. His tenure ended on January 3, 1913 when he resigned his Senate seat. After his defeat by Pat M. Neff in the Democratic gubernatorialprimary in 1920, Bailey moved to Dallas to practice law. In 1929, he died in a courtroom in Sherman, Texas.
