Born in Dallas, Texas, the son of a dentist began his career as a Quarter Horse rider at the age of 12. His Thoroughbred racing career began in 1974, and he primarily rode the New York\Florida circuit.

Bailey rode Fit to Fight in his New York Handicap Triple Crown sweep in 1984 and has ridden four Breeders' Cup Classic winners: Black Tie Affair, the 133-1 Arcangues, Concern, and Cigar. He also won two Kentucky Derbys on Sea Hero and Grindstone.

Bailey's riding skill was amply demonstrated one weekend in 1991 when he brought Hansel home by a head in the Belmont Stakes and Meadow Star home by a nose in the Mother Goose.

More recently, Bailey has been well known for challenging the record of consecutive wins held by Citation. Bailey and Cigar equalled Citation's record of 16 consecutive wins in 1996.

As a former President of The Jockeys' Guild, Bailey was instrumental in lobbying for protective vests to be worn by all riders. He received the George Woolf Memorial Jockey Award in 1992 and was inducted in the National Horse Racing Hall of Fame in 1995.

Bailey has ridden 14 Breeders' Cup race winners - more than any other jockey. He has also been honored eight times with the Eclipse Award as the nation's outstanding jockey, including seven of the nine years from 1995 through 2003. No other jockey has ever received the Eclipse Award more than five times.

Other than Cigar, champions that have been ridden by Bailey include Pleasantly Perfect, My Flag, Soarning Softly, Macho Uno, Orientate, Six Perfections (Fr), Hansel, and Black Tie Affair (Ire).

Back to Honorees List