Jerry Bailey is widely regarded as one of the greatest jockeys of all time and is best known for his unbeatable partnership with the legendary horse Cigar. The duo achieved an amazing 16 win-streak, which was a tie for the modern North American record for consecutive wins in 1995. As the regular jockey of Cigar, they also won the Breeders’ Cup Classic in 1995 and the inaugural Dubai World Cup the next year.
Bailey was able to accumulate 5,894 wins and won $296 million over his 31-year riding career. His earnings were second only to Pat Day at the time of Bailey’s retirement. He won 216 Grade 1 races, which was a record at the time of his retirement, and he won 16 riding titles in New York. He also won 15 Breeders’ Cup races, won each Triple Crown race twice, and had four victories total in the Dubai World Cup.
Bailey’s achievements earned him numerous awards and accolades, starting with the George Woolf Memorial Jockey Award for high standards of personal and professional conduct in 1992. He was awarded the Mike Venezia Memorial Award in 1993, and he was inducted into the National Museum of Racing and Hall of Fame in 1995. Bailey won the first of three consecutive Eclipse Awards for Outstanding jockey in 1995-1997, and then won it four more times in a row from 2000 to 2003, for a total of seven Eclipse Awards. No other jockey has ever received the Eclipse Award more than five times, let alone seven. In 2001, he was named the first jockey to earn over $20 million.
When Bailey retired from racing in January 2006, he ranked second on the career North American money list. His last official race was on January 28, 2006, at Gulfstream Park, but he returned to the saddle one last time in 2008 for the “Living Legends Race” at Santa Anita in which he competed against seven fellow retired Hall of Fame riders to celebrate the 25th anniversary of the Breeders’ Cup. After his retirement, Bailey started a new career as a horse racing analyst for ESPN, then moved to NBC when ESPN discontinued horse racing coverage in 2012.
Demographic Profile
- Born: August 29, 1957 (age 65)
- Place of Birth: Dallas, Texas, United States (raised in El Paso)
- Residence: Currently residing in South Florida.
- Nationality: American
- Height: 1.6 m (5ft 5in)
- Weight: 112 lbs. (50.8 kg)
Racing Career
Mounts | 30, 856 |
Earnings | $296,113, 529 |
Wins | 5,893 |
Debuted | November 2, 1974, at age 17, on Pegged Rate at Sunland |
Retired | January 2006 |
First Win | November 3, 1974, on Fetch |
Major Races
- New York Handicap Triple (1984)
- Jaipur Stakes (1984, 1991, 1993, 1998, 2001, 2002)
- Bonnie Miss Stakes (1993, 1996, 2000, 2001, 2005)
- Dubai World Cup (1996, 1997, 2001, 2002)
- Prince of Wales’s Stakes (2000)
- Hollywood Gold Cup (1992, 1995, 1998, 1999, 2003)
- Pacific Classic Stakes (2004)
- Del Mar Futurity (2000)
- Palomar Breeders’ Cup Handicap (2005)
- Madison Stakes (2005)
- Arkansas Derby (1988)
- Pimlico Special (1995, 1997, 2001)
- Jockey Club Gold Cup (1995, 1997, 2001)
- Arlington Million (2000, 2002)
- Kentucky Oaks (1993, 2001, 2005)
American Classics wins:
- Kentucky Derby (1993, 1996)
- Preakness Stakes (1991, 2000)
- Belmont Stakes (1991, 2003)
Breeders’ Cup wins:
- Breeders’ Cup Juvenile Fillies (1995, 1999)
- Breeders’ Cup Juvenile (1996, 1998, 2000)
- Breeders’ Cup Filly & Mare Turf (1999, 2000)
- Breeders’ Cup Sprint (2001, 2002)
- Breeders’ Cup Mile (2003)
- Breeders’ Cup Classic (1991, 1993, 1994, 1995, 2005)
Historical Achievements, Honors Received, Recognitions
1992
- George Woolf Memorial Jockey Award
1993
- Mike Venezia Memorial Award
1995
- United States Racing Hall of Fame
- United States Champion Jockey by earnings
- Eclipse Award for Outstanding Jockey
- He published his autobiography Against the Odds: Riding for My Life
1996
- United States Champion Jockey by earnings
- Big Sport of Turfdom Award
- Eclipse Award for Outstanding Jockey
1997
- United States Champion Jockey by earnings
- Eclipse Award for Outstanding Jockey
2000
- Eclipse Award for Outstanding Jockey
2001
- United States Champion Jockey by earnings
- Eclipse Award for Outstanding Jockey
2002
- United States Champion Jockey by earnings
- Eclipse Award for Outstanding Jockey
- Saratoga and NYRA honored Jerry Bailey with a bobblehead doll
2003
- United States Champion Jockey by earnings
- Eclipse Award for Outstanding Jockey
Characteristics
Unlike many other jockeys who get into racing due to a love of horses, Jerry Bailey has said that he never really loved horses until he met Cigar. Bailey became a jockey because he enjoyed the thrill of competition more than anything else, and horses were a means to that end. It was only after he teamed up with Cigar that he came to love horses. Even after Cigar retired, Bailey visited him regularly in Lexington, KY, up until the champion horse passed away in 2014. Bailey said of Cigar, “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 is also well-known for his professionalism, athleticism, and strategic mind. The Hall of Fame trainer Bill Mott described Bailey as a dedicated athlete, saying, “He trains hard. He thinks about it, he works at it, he doesn’t smoke, drink or stay up late.” Similarly, Hall of Fame trainer Bobby Frankel has praised Bailey for his cerebral approach to horse racing, saying, “Jerry puts a lot of time and effort into what he does. He’s very well-prepared going into every race. By the time he gets to the paddock, he knows everything there is to know about the horse he’s riding, and he knows everything about the horses he’s riding against.” Trainer Fred Danley has said that Bailey worked horses perfectly and knew how to handle them because he could analyze the horse’s speed and capabilities. In short, Bailey is a smart rider and a skilled handicapper, and he often knew how a race would shape up and what the other riders would do.
This approach earned Bailey a reputation for being aloof at times because he was often so focused on recalling the tactics and analyses he had studied to prepare for a race that he didn’t socialize with anyone beforehand, and he chose not to go out partying with the other jockeys after races. Bailey was candid about this behavior in his autobiography, Against The Odds: Riding For My Life, where he admitted that he struggled with alcoholism, and it nearly cost him both his marriage and his career before he made the decision to quit drinking in 1989.
Although some may have seen Bailey as aloof, most knew him as a compassionate and amiable man with a generous spirit. He donated $19,000 to the Jockeys’ Guild Disabled Fund when he won the Preakness in 1992, and he did it again the next year after winning the Derby. As president of the Jockey’s Guild from 1989 to 1996, Bailey became an official advocate for improved health and safety standards in racing. He also championed the use of flak jackets, protective vests worn by jockeys to protect against injuries to the torso and especially the spine.
Plaque/Statue
The Kentucky Horse Park unveiled a memorial statue dedicated to thoroughbred champion Cigar on October 27, 2015. The statue portrays Jerry Bailey riding Cigar when they won the 1995 Breeders’ Cup Classic. It was sculpted by artist Douwe “Dow” Blumberg and placed at Cigar’s gravesite at the Hall of Champions.
Bailey was the second jockey to have two bobbleheads made in his likeness. The first was made by the New York Racing Association and given away at Saratoga on July 28, 2002. The second was made by Sunland Park in Texas and was given away in several locations, including the Churchill Downs Sports Spectrum facility on February 9, 2003, and Lone Star Park on February 22, 2003.
Personal Life
Jerry Bailey was born in Dallas, Texas in 1957, but grew up in El Paso, West Texas. His farther, Dr. James Bailey, was a dentist that loved horses and horse racing. Bailey always wanted to be an athlete, but his first sport of choice as a child was football. Unfortunately, he wasn’t very successful at football due to his diminutive stature, and he tried a few other sports before he found horse racing. Bailey and his father started watching weekend races together and hanging out in barns, and when Bailey was 12, his father acquired a string of horses and a farm.
Bailey took his first racetrack job at Sunland Park a few years later as a groom for trainer J.J. Pletcher, and an occasional babysitter for Pletcher’s son. He started racing thoroughbreds at 17 years old and participated in his first official race on November 2, 1974, aboard Pegged Rate at Sunland. Although he finished unplaced, he won both his mounts the next day aboard Fetch.
Initially, Bailey was happy just to be competing and didn’t dream of becoming a famous jockey. He thought he’d never leave New Mexico, but he went on to become the leading apprentice jockey at Sunland Park and Ak-Sar-Ben, and rode his first stakes winner, Bye Bye Battle, in the $25,000 His Majesty’s Council Handicap on May 24, 1975, and his father advised him to go to cities with bigger racing to pursue higher earnings. He spent the next several years racing in Chicago and south Florida before he moved to New York in 1982.
Bailey met his future wife, Suzee Chulick, in 1984 after he won the Flamingo Stakes aboard Time For A Change. Chulick was a New York-based reporter for SportsChannel at the time and interviewed Bailey in the Hialeah Park winners’ circle. They were married in December 1985 in Great Neck, New York, and had a son in 1992, Justin Daniel.
Personal Struggles
Although Bailey had his share of winning races in the 1980’s, he still hadn’t reached his full potential as a jockey, and he described his career at that point as “mired in mediocrity.” He divulged in his autobiography that he struggled with a drinking problem for many years, and his most serious riding accidents were the result of dulled reflexes and slowed reaction time from drinking the night before a race. In various spills from 1984 through 1986, he suffered 15 broken ribs, a punctured lung, a broken collarbone, and three cracked vertebrae. His personality suffered as well; even the trainer Mack Miller, who was very supportive of Bailey, was forced to fire him when it became apparent that Bailey had a drinking problem.
On New Year’s Day in 1988, Bailey’s wife Suzzee found him drunk on the floor and told him that he needed to seek treatment. She had always supported him in his struggles, and she called a friend with experience in counseling alcoholics to help Jerry. Bailey entered outpatient care, and on January 1, 1989, he quit alcohol for good. His life drastically changed for the better – his relationship with his wife improved, his thinking was clearer, Miller eventually hired him back, and he found greater success on the track.
The Unbeatable Cigar and the Amazing Arcangues
Arcangues – Breeders’ Cup (1993)
One of the most famously unexpected wins in Breeders’ Cup history occurred in 1993 when Bailey was aboard Arcangues. The odds on the horse were 133-1, a huge long shot, and yet they won in what may be the biggest upset in thoroughbred racing history.
What makes this victory even more astonishing is that Bailey had never even seen the horse before that day or met the trainer, Andrew Fabre. On the day of the race, Bailey couldn’t find Fabre in the paddock, and the colt’s groom only spoke French so Bailey wasn’t able to understand his instructions. Bailey ended up going into the race blind, and when he noticed the oddsboard, he decided that he would need to stay close to the rail for as long as possible to have any hope at breaking into the top five.
However, Bailey became increasingly confident as the race progressed. The favorite, Bertrando, set the early pace and had a good lead coming down the stretch, but Arcangues caught up to him and surpassed him near the wire. This surprising upset resulted in a Breeders’ Cup-record $269.20 payout for a $2 win ticket. Bailey was just as surprised as anyone else, saying, “”I don’t even know how to pronounce the horse’s name. But sometimes a horse runs best when he is ridden by someone who has never been on him before.”
Cigar – The Invincible 16-Win Streak
Out of all of Bailey’s wins, his rides with Cigar were his most memorable, and nothing seemed impossible for the duo during Cigar’s unbeatable win streak. Together, they won 16 consecutive races from October 1994 to the summer of 1996. Cigar and Bailey were launched into fame, and Cigar became known as the “Horse of the World”. Their win streak included victories in the Oaklawn Handicap, Gulfstream Park Handicap, Hollywood Gold Cup, Jockey Club Gold Cup, Pimlico Special, Breeders’ Cup Classic, Woodward Stakes, and the Donn and Massachusetts handicaps.
Cigar earned Horse of the Year honors and Outstanding Older Male Horse in both 1995 and 1996 – he is one of only two Maryland-breds to ever be named Horse of the Year. He was the first American racehorse running against a top-class competition to win 16 consecutive races since Triple Crown winner Citation (between 1948 & 1950), a feat that has only been surpassed once since Cigar by the mare Zenyatta in 2010.
Their incredible win streak ended when they were defeated in Cigar’s 17th race, for which Bailey blames himself. In that pivotal race, Cigar sped through the first mile in the phenomenal time of 1:33 3/5, nearly breaking the world record for this distance. However, Bailey was left in a no-win position where he would either be boxed in or forced to keep up that blistering pace to chase Siphon. Bailey decided to avoid becoming trapped and kept up the pace, but this left Cigar too tired to resist when Dare and Go rallied and pulled ahead to victory.
2004 Controversy
Jerry Bailey (aboard Eddington) was involved in a controversy during the Belmont Stakes in 2004 in which the favorite, Smarty Jones, lost the race and was denied a Triple Crown sweep. No one had won all three Triple Crown races since Affirmed in 1978, and Smarty Jones was wildly popular at the time, having won the Derby and Preakness that year.
Smarty set a lightning-fast pace on the front end but was pressured early on the backstretch by Eddington and Rock Hard Ten. This caused Smarty to surge ahead, but all three horses were unable to keep up the incredible pace in the final 100 yards and started to lag, and Birdstone came from behind with a burst of speed to beat Smarty by a length (Eddington and Rock Hard Ten fell back to finish fourth and fifth, respectively).
Smarty’s trainer, John Servis, blamed Bailey and Alex Solis (jockey for Rock Hard Ten) for his defeat in the race, arguing that they “sacrificed” Eddington and Rock Hard Ten to deny Smarty Jones the win. He claimed that they intentionally kept Smarty Jones running to tire him out and ensure he didn’t win. Of course, such a strategy would have been suicidal for Bailey and Solis, and Bailey has always denied that they ganged up on Smarty Jones. Bailey said that Smarty Jones simply got tired and was beaten, adding, “I’m sorry he feels that way, but that’s not the case.”
Although Servis and owner Roy Chapman still maintained that they were targeted, Bailey defended his tactics as being necessary for him to have a chance at winning against Smarty. In the end, the simplest explanation is the most likely: Smarty came from a miler/sprinter pedigree and running style and just wasn’t capable of keeping up such a blistering pace for the long 1 ½ mile track at Belmont.
After Retirement
Jerry announced his retirement on January 19, 2006, and had his final race at Gulfstream Park on January 28, 2006. He believed it was the right time to retire and wanted to spend more time with his family. On January 24, before his last race, he announced that he would move from the saddle to the TV set and become an analyst with ESPN and ABC Sports. When ESPN stopped horse racing coverage in 2012, Bailey joined NBC as their horse racing analyst.
Notable Horses Mounted
Black Tie Affair, Sea Hero, Fit to Fight, Cigar, Arcangues, My Flag, Skip Away, Royal Anthem, Hansel, Real, Quiet Six Perfections, Dubai Millennium, Grindstone, Concern, Congaree, Victory Gallop, Medaglia d’Oro, Candy Eclair, Empire Maker, Saint Liam