The history of horse racing is full of memorable jockeys, including Sir Tony McCoy, Russell Baze, Frankie Dettori, and John Velasquez. Horse racing bettors and casual fans can learn more about them in this top 10 list created by BetZillion’s team. The rankings were based on active jockey years, earnings, and career wins.
Sir Antony Peter McCoy, popularly known as AP McCoy or Tony McCoy, is recognized as the most successful jockey in jump racing. Born in Ireland, McCoy recorded his first win at the age of 17 in a flat race at Thurles racecourse. He soon started competing at English tracks and continued to win.
During his illustrious career, McCoy won all major National Hunt races. This includes the Grand National, Cheltenham Gold Cup, Queen Mother Champion Chase, and the Champion Hurdle. He holds a record with 20 consecutive British Jump Racing Champion Jockey titles, won between 1995/96 and 2014/15. McCoy also became the first jockey to win BBC Sports Personality of the Year in 2010.
Another major highlight of Tony McCoy’s career happened in December 2013, when he officially became a Guinness World Record holder in three categories. McCoy was awarded records for most winners in a season (289 jump wins in 2001/2002), most Champion Jump Jockey titles (18), and the most career jump winners (4,022). He would go on to improve records in the latter two categories, winning two more titles and bringing his career total of jump winners to 4,348.
McCoy retired in 2015 with 4,358 career wins in jump and flat races. He was knighted in 2016 for his services to horse racing.
Ruby Walsh is the third most successful winner in the history of British and Irish racing behind Sir Tony McCoy and Richard Johnson. A son of an Irish amateur jockey turned racehorse trainer, Walsh claimed consecutive Irish amateur titles in 1996/97 and 1997/98 before going pro. In 2000, at the age of 20, he won the English Grand National. It was his first time competing, and he did it atop a horse trained by his father.
Ruby Walsh would go on to add more impressive achievements to his name. He has been the Irish Jump Jockey champion 12 times. Walsh is also the most successful jockey at the Cheltenham Festival. He achieved a record 59 wins from 2004 to 2017 and earned the meeting’s leading jockey award 11 times.
Walsh received the Horse Racing Ireland National Hunt award for five consecutive years (2004- 2008) and won three Lester Awards in the International Jockey of the Year category. He announced his retirement in 2019 after a 24-year career that delivered 2756 wins.
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Russell Avery Baze is one of the most successful and famous jockeys in North America’s horse racing history. Born and raised in a horse racing family, he started his career in 1974. As a 16-year-old, he won his first race at the Yakima racetrack.
During his illustrious career, Baze became a 13-time United States Champion Jockey by wins. He won 40 titles at Bay Meadows racetrack and 54 riding championships at Golden Gate Fields. But arguably the biggest highlight of Baze’s career came in 2006 when he broke Laffit Pincay Jr’s record for most career victories. In April 2010, he achieved a personal milestone with a win at the San Francisco Breeders’ Cup Mile, a prestigious race at the Golden Gate Fields that had always eluded him.
Russel Baze is a member of the National Museum of Racing and Hall of Fame, being inducted in 1999. He retired in 2016 at 57 with 12,844 wins, stamping his status as North America’s all-time winningest jockey.
Laffit Pincay Jr. got into horse racing thanks to his father, who competed as a jockey at racetracks in Panama and Venezuela. In 1966, renowned horseman Fred W. Hooper took Pincay to the United States and gave him a riding contract that paid $500 a month. He got his start in America at Arlington Park and promptly demonstrated his talent by taking 11 mounts and winning eight races. He quickly gained nationwide recognition and secured riding titles and major stakes on both the East and West coasts.
During his long career, Pincay won almost every major US race. This included triumphs at the Kentucky Derby and Belmont Stakes, two out of three American Classics. He was the United States Champion Jockey by Wins in 1971 and claimed seven titles as the United States Champion Jockey by Earnings. In 1975, Pincay was also inducted into the National Museum of Racing and Hall of Fame.
With his 8,834th win in December 1999 at California’s Hollywood Park Racetrack, Pincay overtook Bill Shoemaker’s record to become the winningest jockey in the world. He still held on to this title in 2003, when he retired with 9,530 career wins. The record was later broken by Russel Baze.
Frankie Dettori was introduced to horse racing by his father, Gianfranco, who was a 13-time Italian Champion jockey. When Dettori was nine, he rode in the Pony Derby at the San Siro Racecourse. At the age of 13, he quit school and started working in the racing stables to chase a career as a jockey. He later relocated to England to serve as a jockey apprentice.
As a teenager, Dettori started making his mark on the horse racing scene. By the time he turned 18, he became the first teenager to have won 100 races in a season since Lester Piggott. He won three British Champion Jockey titles and holds the record with six wins at France’s Prix de l’Arc de Triomphe. However, the achievement that made Dettori one of the greatest and most famous horse jockeys happened in 1996. He won all seven races, riding seven different horses, at the British Festival of Racing at Ascot. The feat, which became known as “Magnificent Seven,” remains unmatched.
Frankie Dettori has had an incredibly remarkable career, winning horse races in Italy, Britain, the United States, Ireland, France, Germany, and the United Arab Emirates. He is active to this day, competing at racecourses in North America.
Lester Piggott, nicknamed “The Long Fellow” due to his tall stature, was an English professional jockey and trainer. He is credited with developing a unique race-riding style that was later imitated by numerous other riders. Born into a long lineage of jockeys and trainers, Piggott won his very first race in 1948 at Haydock Park when he was 12. By his teens, he was already a sensation in horse racing and became the youngest jockey to win over 100 races in one season.
During his career, Piggott won just about every worthwhile race in the United Kingdom. He was dominant in prestigious Grade 1 races, including the Epsom Derby (9 wins), Ascot Gold Cup (11 wins), July Cup (10 wins), and the Coronation Cup (9 wins). He also raced internationally, winning the Prix de l’Arc de Triomphe (France), Irish Derby (Ireland), and Derby Italiano (Italy).
Piggott was the British flat racing Champion Jockey 11 times and won thirty British Classic races from 1954 to 1992. The Lester Award, which recognizes the best jockeys in flat and jump racing since 1990, was named in his honor.
Lester Piggott officially retired in 1995 as one of the greatest flat racing jockeys ever, with 4,493 domestic career wins under his belt. He also recorded 850 wins internationally. In 2021, Piggott became one of the first two entries in the British Champions Series Hall of Fame.
John R. Velazquez started his horse racing journey by attending jockey school in native Puerto Rico. He won his first race in 1990 at the El Nuevo Comandante racetrack in Canóvanas. Velazquez moved to the United States that same year to receive guidance from renowned leading jockey Angel Cordero Jr. Soon after, Velazquez won his first stake race at the Aqueduct Racetrack. His first graded win came a year later at the Ohio Derby, and things only went up for him since then.
During his illustrious career, Velazquez won several major graded stakes, including the Kentucky Oaks, Dubai World Cup, and Woodbine Mile. He is a 15-time Breeders’ Cup winner and was triumphant at all US Triple Crown races, including the Kentucky Derby (3 times), Belmont Stakes (2 times), and Preakness Stakes (once).
Velazquez was the United States Champion Jockey by Earnings in 2004 and 2005, while also receiving the Eclipse Award for Outstanding Jockey in both of those years. He was inducted into the National Museum of Racing and Hall of Fame in 2012. Velazquez is still active in the horse racing scene and has over 6,700 career wins through 2025.
Mike E. Smith grew up on his maternal grandparents’ horse farm, where he began breaking horses at a young age. At 11, Smith started racing horses in New Mexico and got a jockey’s license when he was 16. He soon quit school and began riding the Midwestern circuit. In 1991, Smith made the list of the few American jockeys to have won a European classic by winning the Irish 2,000 Guineas. He also established himself as the leading jockey at New York tracks, recording the most wins for three straight years (1991-1993).
Throughout his career, Smith recorded wins at various prestigious races, including:
In 2018, Smith became the oldest jockey to win the Triple Crown at age 52. A year after that, Smith achieved another incredible milestone by surpassing Jerry Bailey for most Grade 1 wins in North America, with 217 victories.
As one of the leading jockeys in US Thoroughbred racing since the 1990s, Smith has received several awards and honors, including two Eclipse Awards for Outstanding Jockey. In 2003, he was inducted into the National Museum of Racing and Hall of Fame. As of 2025, Smith has 5,786 career wins.
Sir Gordon Richards is widely considered to be one of the best jockeys in history. He was passionate about the sport from an early age, riding pit ponies raised by his father. In 1920, he participated in his first race at age 16 at Lincoln racecourse. His first win came a year later at Leicester, and Richards soon became a sensation in horse racing. He won five British Classics multiple times and was triumphant at almost all other major races in the UK.
During his long career, Sir Gordon Richards was Champion Jockey 26 times. This feat stands to date and may never be equaled. In 1931, Richards broke Fred Archer’s long-standing record of the most wins in a season with 259 victories. The record stood for more than 70 years before Tony McCoy topped it in 2002. Richards was also the first jockey to be knighted and remains the only flat racing jockey with this honor.
Richards retired in 1954 after an injury with 4,870 career wins to his name. He later became a trainer and was quite successful before he died in 1986.
Regarded as one of the greatest and most famous horse jockeys ever, William (Bill) Shoemaker has always been a fighter by nature. He weighed roughly one kilo at birth and was not expected to make it through the night. But not only did Shoemaker survive, he also went on to become a giant in thoroughbred racing.
Shoemaker started riding professionally in 1950 at the age of 18, achieving his first victory at Golden Gate Fields. A year later, Shoemaker clinched the coveted title of the United States Champion Jockey by wins. He would later achieve this feat four more times.
Over the course of his career, Shoemaker won all the American Classic races multiple times and the Breeders’ Cup Classic in 1987. Sadly, the highly coveted Triple Crown itself eluded him. To date, he is the jockey with the most wins in several major races, including the Hollywood Derby (8 wins), the Del Mar Handicap (8 wins), and the Santa Anita Handicap (11 wins).
Shoemaker won the Eclipse Award for Outstanding Jockey in 1981 and was the United States Champion Jockey by earnings 10 times. He was also inducted into the National Museum of Racing and Hall of Fame in 1958.
Shoemaker officially hung up his spurs in 1990 with 8,833 wins to his record. He later returned to the track as a trainer until his death in 2003.
The Kentucky Derby, also known as “The Most Exciting Two Minutes in Sports” and “The Run for the Roses,” is among the world’s most prestigious and highly anticipated horse racing events. Held annually on the first Saturday in May at Churchill Downs in Louisville, Kentucky, the Derby is an American Grade 1 stakes run by three-year-old Thoroughbreds. This iconic race is one of the three classic American races comprising the highly coveted Triple Crown.
A race with a rich history dating back to 1875, the Kentucky Derby has witnessed 107 different winning jockeys. 27 of them managed to claim the Kentucky Derby Trophy multiple times, including John R. Velazquez, Bill Shoemaker, and Bill Hartack.
John R. Velazquez made his debut at the Kentucky Derby in 1996, finishing last. In 2001, he came close to winning the race but ended in second place. After 12 unsuccessful rides, he recorded his first Kentucky Derby win in 2011 atop Animal Kingdom. He only took part in the race because Animal Kingdom’s original jockey, Robby Albarado, was injured several days before.
Velazquez would go on to win two more Kentucky Derbys. His next win came in 2017, while riding Always Dreaming. He managed to make his Kentucky Derby hat trick in 2020 aboard Authentic.
Velazquez crossed the finish line first at the 2021 Kentucky Derby as well. However, the win was later taken away from him after his horse, Medina Spirit, was disqualified.
Bill Shoemaker’s series of wins at the Kentucky Derby started in 1955 when he took first place aboard Hall of Famer Swaps. Shoemaker narrowly lost his next shot at a Derby win to Bill Hartack in 1957 when he reigned in his horse too early, having misjudged the finish line. His second win eventually came in 1959 atop Tommy Lee.
Shoemaker’s third win came six years later, in 1965, while riding Lucky Debonair. He clinched his fourth and final Kentucky Derby win aboard Ferdinand in 1986.
His last win was a memorable one. Shoemaker overcame 17-1 odds while having to fight back from a poor starting position. At the age of 54, he also became the oldest jockey to win the Kentucky Derby.
Bill Hartack (full name William John Hartack Jr.) is the winningest jockey in the Kentucky Derby alongside Eddie Arcaro. Both Hartack and Arcaro won the prestigious race five times.
Born in Pittsburgh, Pennsylvania, in 1932, Hartack started his career as a jockey in his teens. He was only 19 when he first won a race at Waterford Park, a West Virginia minor league track. Hartack won his first Kentucky Derby in 1957 atop Iron Liege. It became one of the most famous moments in Derby racing history as Iron Liege won against Gallant Man by a nose. Bill Shoemaker, the jockey atop Gallant Man, supposedly misjudged the finish line and stood up in his stirrups too soon, allowing Hartack to make a late comeback.
Hartack’s next Kentucky Derby win came three years later, in 1960, atop Venetian Way. He completed a hat trick in 1962 with a dominant performance aboard Decidedly.
In 1964, Hatrack recorded his fourth win while riding Northern Dancer. Before this race, many believed Northern Dancer didn’t have the stamina to endure the race’s distance due to its small size. But the horse delivered an impressive performance, ultimately winning by a neck. Hartack’s fifth and final win at the Kentucky Derby came in 1969 aboard Majestic Prince.
Hartack’s other notable wins include Preakness Stakes (1956, 1964, 1969) and Belmont Stakes (1960). He was also a four-time United States Champion Jockey by wins and a two-time United States Champion Jockey by wins. In 1959, Hartack became a member of the National Museum of Racing and Hall of Fame.
This concludes our betting whiz list of the winningest and most famous horse jockeys of all time. It shows that the horse racing world has been graced by remarkable riders who have made a lasting mark on the sport.
From the legendary Bill Shoemaker to the iconic Sir Gordon Richards and Russell Baze, these jockeys have shown unmatched skills on the racetrack. They etched their names in the history books with spectacular achievements that deserved to be remembered and honored.
If this list prompted you to consider placing bets on the best jockeys, make sure to first check out our live in-play betting tips.
