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.
Jerry Bailey’s Analytical Approach to Race Riding
Jerry Bailey’s two Eclipse Award victories as Outstanding Jockey and his exceptional record in major stakes races reflected a riding style that was perhaps more analytically driven than that of most of his contemporaries. Known for his ability to assess race situations quickly and make decisive tactical adjustments, Bailey approached each race with a clear plan while maintaining the flexibility to adapt when the pace or position of other horses deviated from what he had anticipated. This combination of preparation and adaptability — doing the mental work before the race while staying present and responsive during it — is a quality that the best jockeys in any era share.
His career commentary and television analysis work after retiring from the saddle have given racing fans and bettors unique insights into how an elite rider thinks about race-riding decisions. The ability to articulate tactical reasoning — explaining why a specific move at a specific point in a race was the right or wrong choice — reflects a genuine analytical understanding of the sport that translates directly into the kind of insights bettors can use to improve their own assessment of how races are likely to unfold. For more on elite American jockeys and their riding approaches, our profiles of Angel Cordero and “Bill” Shoemaker cover other analytical riding legends. And our guide to betting jockeys in horse racing covers how to use jockey knowledge practically.
