Jerry D. Bailey (born August 29, 1957) is a retired American Hall of Fame jockey and current NBC Sports thoroughbred racing analyst. He is widely regarded as one of the greatest jockeys of all time.
Bailey was born in Dallas, Texas but raised in El Paso. 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. He began riding Quarter horses at the age of 12 and started riding Thoroughbreds competitively at 17 in 1974.
Bailey took his first racetrack job at Sunland Park as a groom for trainer J.J. Pletcher and an occasional babysitter for Pletcher's son, Todd, then in the second grade, who later would follow in his father's footsteps and eventually become one of America's most successful trainers.
Bailey's first official ride came on November 2, 1974, on Pegged Rate at Sunland. That horse finished unplaced, but Bailey won with both his mounts the next day, scoring his first career victory aboard Fetch. He had no grand ambitions: "I didn't think I'd ever leave New Mexico", he told an ESPN interviewer.
The next year, Bailey was the leading apprentice jockey at Sunland and Ak-Sar-Ben, where he rode his first stakes winner, Pletcher-trained 3-year-old filly Bye Bye Battle, in the $25,000 His Majesty's Council Handicap on May 24, 1975. 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.
In the fall of 1976, Bailey moved to the south Florida circuit of Calder Race Course, Gulfstream Park and Hialeah Park, and over the next few years also raced at Hollywood Park, Monmouth Park, Hawthorne Race Course and Arlington Park. In 1982, Bailey began riding regularly at the major New York tracks – Belmont Park, Aqueduct Racetrack, and Saratoga – while returning to Florida in the winters, a popular circuit he would continue riding the remainder of his career, and would later dominate.
Regarded as one of the world's all-time greatest jockeys, Bailey's mounts won 5,894 races and more than $296 million during a 31-year riding career, second only to jockey Pat Day at the time of Bailey's retirement.
At the time of his retirement in January 2006, he ranked No. 2 on the career North American money list and still ranks No. 3. 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 earned a record four victories in the Dubai World Cup, the world's richest race, and is the only jockey ever to win America's Eclipse Award for Outstanding Jockey seven times, including an unprecedented four straight years (2000–2003).
Bailey had many prominent mounts, but will be best remembered as the regular jockey of Cigar, who tied the modern North American record for sixteen consecutive wins, including an undefeated Horse of the Year campaign in 1995, capped by a win in the Breeders Cup Classic. The next spring, jockey and horse teamed to win the inaugural Dubai World Cup. After Cigar retired to stud, Bailey visited him regularly in Lexington, Kentucky, up until he died in 2014. Bailey said, "He was just a cool horse. He was charismatic and he loved people. We know how good he was on the track, how he dominated horses. I was just always interested in what he was doing at the barn."
Bailey was inducted into the American Racing Hall of Fame in 1995. 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. Bailey also won the All-Star Jockey Championship in 2001 and 2004 at Lone Star Park.
Bailey's 1993 win in the Classic, riding French horse Arcangues, ranks as one of the biggest upsets in Thoroughbred racing history. The races were held at the Santa Anita Derby. Arcangues was a tremendous long shot. Bailey had never before ridden Arcangues and was given the ride only nine days before the race. The colt's groom tried to give Bailey instructions in French in the paddock, and Bailey was able to speak only briefly to trainer André Fabre while he was already on Arcangues' back in the walking ring. He had to determine his own race plan. Bailey glanced at the odds board during the post parade and decided he needed to stay close to the rail as long as possible in hopes of cracking the top five positions on the board. Arcangues stormed past favorite Bertrando in the stretch to win comfortably at 133-to-1 odds, paying a Breeders' Cup-record $269.20 for a $2 win ticket. (The odds were so high the tote board at Santa Anita Park could not encapsulate them, reading 99-to-1.)
Bailey described the two-minute race on video later. Among his comments:
When...I broke from the gate, all I did was just ease him back a little bit, try to find a rhythm with him. I had no idea what to expect. My expectations were actually very, very low. ... I had three or four horses beaten, and...I was pleased here, I thought, "This horse is not going to embarrass me." ... Bertrando was on the lead... I've got a lot of horse, and I'm thinking, "Not only can I hit the board, I may actually have a chance to win this thing." ... Arcangues was full of run when I asked him. We went past Bertrando as easy as you can go by a horse. I knew Gary Stevens was probably thinking, as he looked up, "Who in the heck is this horse running by me?" At this point, Arcangues went on and won easily. A shocker.
About Arcangues, "I still don't know how to pronounce his name," Bailey joked afterwards. 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. In 2023, the website America's Best Racing rated it at #1 of "14 Amazing Upsets in the Breeders' Cup." Essentially Sports writes that "his 1993 Breeders Cup win was one-of-a-kind and will forever go down in the annals of history for being his most legendary [win]." The announcer for the race, Tom Durkin called it an "absolutely shocking, impossible victory."
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. Included in his 2003 victories were 26 wins in Grade 1 stakes races, a record that still stands. Fourteen of those Grade 1 victories were on horses trained by Frankel, including Empire Maker, Medaglia d'Oro, Sightseek and Aldebaran.
Through his own words and actions, Bailey was most fond of riding in the summers at Saratoga Race Course – America's most prestigious race meeting. "I am worn out at the end of (Saratoga)", Bailey once said. "I try to pace myself all year to get ready for that one meet." 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. On August 6, 2004, Bailey rode Taittinger Rose to his 641st Saratoga victory, surpassing Cordero's career record – although Cordero's totals were remarkable considering Saratoga raced only 24 days a year until 1991. Bailey's career total of 693 Saratoga wins lasted until broken in 2013 by Velazquez – whose agent is Cordero.