Among those who ride thoroughbreds there are jockeys and there are legends. Jerry Bailey is definitely in the legend category. Bailey won an astounding 5,893 races and $283 million in purse money during a career that spanned 31 years. At the time of his retirement in 2006, Jerry Bailey ranked in the number two spot on the North American racing money list and still sits at number three. His accomplishments are likely to stand for many years due to the longevity of his racing career.
Born in 1957 in Dallas, Texas, Bailey became interested in racing at the age of 11. Bailey’s father, a dentist in El Paso, decided to claim some horses that were racing in New Mexico at Sunland Park. A few years later Bailey took a job as a groom for the racing stable of J. J. Pletcher, a prominent trainer and Sunland and the father of one of the most successful thoroughbred trainers of the modern era, Todd Pletcher. Bailey would sometimes babysit young Todd. Like so many before him Jerry Bailey’s experience as a groom birthed a desire to ride horses and in November of 1974 he had his first mount at Sunland aboard Pegged Rate. The horse did not place but the following day Bailey scored his first of many wins on Fetch. At the time Bailey had little ambition to ever leave the New Mexico racing circuit.
His riding skills quickly developed, however, and Bailey claimed apprentice riding titles at Sunland Park and the very competitive Oaklawn in Hot Springs, Arkansas. Trainers began to take notice of how well Bailey handled a horse and began to put him on better horses. After a short break to attend college in El Paso and stints at tracks throughout the Midwest, Bailey landed in the circuit that would help establish him as an all-time great among jockeys. From 1982 until the end of his racing career Jerry Bailey dominated the New York tracks. At Aqueduct, Belmont, and Saratoga he was a constant force to be reckoned with and piloted some of the most famous racehorses to ever compete.
In the early 1990’s Jerry Bailey would become forever linked with the name of Cigar, one of the winningest horse in the history of racing. After taking over the reins from jockey Mike Smith in Cigar’s four-year-old year, Bailey and trainer Bill Mott steered Cigar through a campaign that included an amazing 16 consecutive wins and 11 Grade 1 stakes victories. Bailey and Cigar also claimed the inaugural running of the Dubai World Cup.
Bailey’s life has not been without its share of controversy. He battled alcoholism for many years before becoming sober in 1989. In the 2004 Belmont Stakes many racing fans criticized Bailey for his ride on Eddington. In the race Bailey and Eddington, a horse with little chance of winning the race, joined Alex Solis and Rock Hard Ten in putting early pressure on Smarty Jones. Smarty Jones was vying for the Triple Crown as a 1-9 favorite and wound up losing the race to Birdstone after the early speed duel. Bailey has defended his performance in the 2004 Belmont by stating that the only chance Eddington had was to pressure Smarty Jones early.
A member of the National Racing Hall of Fame, Bailey can now be seen providing color commentary for NBC’s racing coverage.