He had a pony as a child and became interested in thoroughbred racing at age 11 when his father, James, a dentist, claimed some horses at nearby Sunland Park Racetrack in New Mexico.
After briefly attending college that fall at the University of Texas at El Paso, Bailey returned to the saddle to be leading apprentice at Oaklawn Park in 1976.
He won each Triple Crown race twice (his winning Kentucky Derby rides through traffic on Sea Hero in 1993 and Grindstone in 1996 are considered two of the best in modern Derby history); and scored a record five wins in the Breeders' Cup Classic, the richest race in the U.S., along with other Breeders' Cup categories, totalling 15 victories in all, a record Bailey shares with only Hall of Fame jockey Chris McCarron.
He was chosen by his peers to receive the George Woolf Memorial Jockey Award in 1992, which honors riders whose careers and personal character earn esteem for the individual and the sport of racing.
In 1993, he received the Mike Venezia Memorial Award, honoring jockeys who exemplify extraordinary sportsmanship and citizenship, from the New York Racing Association.
[4] The Total Horse Channel calls it iconic, one of "four of the best moments that fans still remember," on a par with the Belmont Stakes win of Secretariat in 1973.
"[13] From a statistical perspective, Bailey's best season in the saddle was 2003, due in large part to his growing association with late trainer Robert Frankel, whose stable during that time was one of the most formidable in the modern history of the sport.
That year, Bailey won a career-high $23,354,960 million in purses, a North American record that stood until broken in 2012 by Ramon Domínguez.
Fourteen of those Grade 1 victories were on horses trained by Frankel, including Empire Maker, Medaglia d'Oro, Sightseek and Aldebaran.
His seven Saratoga riding championships – second only to Ángel Cordero Jr.'s 14 titles – came in an eight-year span between 1994 and 2001, a streak interrupted in 1998 when John Velazquez topped the standings.
Bailey's most enduring and successful professional relationships were with Hall of Fame trainers MacKenzie Miller, Bill Mott and Frankel, and with Sheikh Mohammed bin Rashid al Maktoum, the ruler of Dubai who with his brothers and family operates a global racing and breeding powerhouse.
That friendship would pay off handsomely in July, when Bailey watched a Del Mar race in which Frankel-trained turf star Chester House lost a stakes he should have won.
[citation needed] Bailey had won only one previous stakes race for Frankel nearly four years earlier, but asked Anderson to contact the trainer and try to get the mount.
Three weeks later, Bailey gave what he called one of the best rides of his life on Chester House in an Arlington Million win that would be the horse's final race.
Together they had a gaudy win rate of 38% in graded stakes races, teaming to take 32 Grade 1s in a five-year span with Flute, Lido Palace, Squirtle Squirt, Aptitude, You, Beat Hollow, Medaglia d'Oro, Empire Maker, Sightseek, Aldebaran, Denon, Spoken Fur, Wild Spirit, Peace Rules, Intercontinental and I'm the Tiger.
Among their many successes were the Belmont Stakes (Empire Maker), Kentucky Oaks (Flute) and Breeders' Cup Sprint (Squirtle Squirt).
Bailey rode Godolphin's Worldly Manner to a seventh-place finish in the 1999 Kentucky Derby, giving up the mount on winner Charismatic, whom he had ridden two weeks earlier to win the Lexington Stakes at Keeneland.
In 2000, Sheikh Mohammed flew Bailey to England to ride Godolphin Racing superstar Dubai Millennium in the Prince of Wales's Stakes at Royal Ascot after regular stable rider Frankie Dettori was injured in a plane crash three weeks earlier in Newmarket.
Bailey teamed with the Maktoums to win the $6 million World Cup in 2002 on Godolphin's Street Cry, when Dettori decided to ride the stable's Sakhee instead.
With Bailey's retirement looming in three weeks, he took a January 7, 1996, mount at Gulfstream Park on Bernardini, owned by Sheikh Mohammed's Darley Stable.
Bernardini then reeled off six straight wins, including the Preakness Stakes, Travers Stakes and Jockey Club Gold Cup, ending his championship 3-year-old season and his career with a second-place finish in the Breeders' Cup Classic to Invasor, owned by Sheikh Mohammed's brother, Sheikh Hamdan bin Rashid Al Maktoum.
Bailey was vilified by many racing fans for his ride on Eddington in the 2004 Belmont Stakes, which Birdstone won with a late surge to deny wildly popular Smarty Jones a Triple Crown sweep.
Smarty Jones was pressured early on the backstretch of the mile-and-a-half race by Bailey from the outside and from the inside by Alex Solis aboard Rock Hard Ten.
That pressure caused Smarty Jones to impatiently rush to the front with jockey Stewart Elliott, and he blew a 3½-length lead entering the stretch to lose by a length.
They joined four other riders as plaintiffs in a suit against the Kentucky Horse Racing Authority, whose prohibition on such patches they alleged to be a violation of their First Amendment rights.
His farewell mount was January 28 in a $500,000 stakes at Gulfstream Park aboard Silver Tree – fittingly for Mott, former trainer of Cigar.
Bailey's final mount as a jockey would actually come on October 18, 2008, at Santa Anita in the "Living Legends Race", in which he joined seven fellow retired Hall of Fame riders to celebrate the 25th anniversary of the Breeders' Cup.
Mounts were selected by random draw for the seven-furlong allowance sprint, which was open to pari-mutuel betting and thus considered an official race and not an exhibition.
[2] Bailey met New York-based SportsChannel reporter Suzee Chulick when she interviewed him in the Hialeah Park winners' circle after his victory in the 1984 Flamingo Stakes with Time For a Change.
In Bailey's autobiography, Against the Odds: Riding for My Life, which he co-wrote with USA Today's Tom Pedulla, he chronicled in great detail his battle with alcoholism that nearly cost him his marriage and his career.