Top 10 Jockeys from the last 50 years

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Javier Castellano is an exceptional jockey from Venezuela who won two out of three Triple Crown races this year (2023), in addition to winning awards, accolades, and thousands of races over the last 20 years. He is the only jockey to have won seven Travers Stakes races, using just 14 mounts to do so, and he’s one of only two jockeys to win four consecutive Eclipse Awards. The winner of 12 Breeders’ Cup races, Castellano has ranked in the top three jockeys by national earnings from 2011 to 2019 and is currently ranked second in all-time earnings (behind John Velazquez) with over $394 million with 5,732 career wins. Javier has also won two Preakness Stakes (2006 & 2017) and the 2016 Kentucky Oaks.

Castellano topped all North American riders in earnings in his Eclipse Award-winning years (2013, 2014, 2015, 2016) and led the national standings in wins in 2013 and 2015. He set a record of $28.1 million in earnings in 2015. Castellano has found success at a multitude of tracks over the years: he has won 11 riding titles on the New York Racing Association circuit, five at Gulfstream, and two at Keeneland. Out of his 11 New York riding titles, six were at Belmont, three at Aqueduct, and two at Saratoga. His five titles at Gulfstream were in consecutive years (2011-2016), and his 132 wins at Gulfstream during the 2013-2014 winter meet set a track record.

In 2017, Castellano was inducted into the National Museum of Racing and Hall of Fame. He was awarded the George Woolf Memorial Jockey Award in 2023, an award based on a nationwide vote of riders that reflects both exceptional career achievements and personal character.

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John Velazquez, or Johnny V, is one of the most accomplished jockeys in the history of racing. Originally from Puerto Rico, he moved to the US in 1990 and was mentored by Hall of Fame jockey Angel Cordero, Jr. Velazquez is famous for being the all-time winningest jockey at Saratoga, surpassing even Angel Cordero, Jr. and Jerry Bailey. He has the second most wins in the Breeders’ Cup out of any jockey and has consistently ranked in the top 10 on the national earnings list for jockeys; he held first place on the list in 2004 and 2005.

Velazquez joined the NYRA circuit in 1990 and Cordero immediately recognized his talent and took him under his wing. Velazquez earned his first riding title at Aqueduct in 1996, and went on to win a total of 26 riding titles at New York tracks. In 2004 and 2005, he was both the United States Champion Jockey by earnings and the winner of the Eclipse Award for Outstanding Jockey. Johnny was inducted into the Horse Racing Hall of Fame in 2012, rode his 5,000th winner in 2013, and became the leading money-earning jockey in the sport’s history in 2014. He is a three-time winner of the Bill Shoemaker Award for top Breeders’ Cup performance (2004, 2011, and 2014). Velazquez has 20 Breeders’ Cup wins, including his first Classic in 2020 with Authentic, three Kentucky Derby wins, two Belmont Stakes wins, and he won the Preakness in 2023.

Velazquez earned his 6,000th North American victory at Aqueduct Racetrack on November 30, 2018. In October 2020, Velazquez became the first rider to win 2,000 races at Belmont Park, and he became the first to win 1,000 races at Saratoga on August 25, 2022. As of 2023, he has 6,551 wins total in his racing career and shows no signs of stopping.

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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.

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One of the hardest decisions for a jockey to make is to retire unwillingly due to an injury at the prime of their career. Ramon Dominguez is a legendary jockey from Venezuela that had to make this difficult decision after he had already accomplished so much in his 17 years of racing, but his love of horse racing is such that he was able to pick himself up after the accident and he has continued to contribute to the horseracing industry in many ways.

A talented and determined jockey, Dominguez was a force to be reckoned with on the track, and during his career he won 4,985 races, including 160 graded stakes races. He won the Breeders’ Cup in three separate years (2004, 2011, and 1012) and has won six races in a single day on four separate occasions. He set a new record for single-season earnings by a jockey in 2012 when his mounts brought in $25,582,252, and his total purse earnings are a whopping $191,620,277. He earned three consecutive Eclipse Awards as the top rider in North America (2010, 2011, and 2012), and he was also the champion jockey in earnings for three consecutive years from 2010 through 2012. On his home circuit in New York, he was the leading rider for four consecutive years (2009 to 2012). In 2012, Dominguez set the track record at Saratoga for the most wins in a single meet with 68 wins.

Dominguez is also known for his class, humility, and professionalism. He was recognized for his excellent conduct by his peers with the George Woolf Memorial Jockey Award from Santa Anita Park in 2012. After Dominguez retired in 2013, he became the first Venezuelan in history to be inducted into the prestigious National Museum of Racing and Hall of Fame. He also joined Delaware Park Wall of Fame colleagues Chris McCarron, William Hartack, Eldon Nelson, William Shoemaker, Eddie Arcaro, and Angel Cordero Jr. In 2017, Dominguez earned a Red Jacket when he was inducted into the Saratoga Walk of Fame. Jerry Bailey, Angel Cordero Jr., and John Velazquez are the only other former jockeys to receive this award.

Post-retirement, Dominguez has stayed active in horse racing in several ways. He invented the 360 Gentle Touch riding crop that is considered to be much safer on horses and is now widely used in horse racing. He was the president of the New York Race Track Chaplaincy and a part of the Permanently Disabled Jockeys Fund (PDJF). Dominguez is an ambassador for the international equine welfare charity Brooke USA, and also has a Spanish YouTube channel on horse racing called Exacta Box.

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Lanfranco “Frankie” Dettori is an Italian horse racing jockey best known for his jaw-dropping “Magnificent 7” feat on September 28, 1996, where he rode all seven winners at the British Festival of Racing at Ascot. Although Dettori found success at an early age, his life has been a rollercoaster of highs and lows: he bounced from being one of the best jockeys to a suspension for substance use, then became a champion again, had a near-death experience, suffered from depression followed by another suspension, appeared in a couple TV series, and finally came back again as a leading jockey.

Dettori was crowned the British champion apprentice in 1989 and he became the first apprentice to ride more than 100 winners since Lester Piggott. He has thrice been a British flat racing Champion Jockey and has ridden the winners of more than 500 Group races. He won seven British Classics, seven Ascot Gold Cup successes, and 14 Breeders’ Cup races. Frankie almost repeated his legendary Magnificent 7 in 2019 when he won the first four races on day three, but he wasn’t able to keep this streak going and lost the fifth race. He also won the Ascot Gold Cup three consecutive times aboard Stradivarius (2018-2020) and won the King George VI and Queen Elizabeth Stakes three times aboard Enable (2017, 2019, and 2020).

Dettori’s Magnificent 7 at Ascot was commemorated in a painting by the noted equine artist Barrie Linklater, commissioned by the Ascot Authority. He was the subject of a 1998 episode of This Is Your Life and a team captain on A Question of Sport from 2002 to 2004. He announced that he would retire after the 2023 racing season, but reversed his decision in October that year after a successful farewell season, and plans to start a new adventure racing in America at Santa Anita for the rest of 2023.

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Ángel Tomás Cordero Jr. is the first Puerto Rican to be inducted into the United States Racing Hall of Fame and to win the Kentucky Derby, Preakness Stakes, and Belmont Stakes, although in separate years. Cordero is the most successful Puerto Rican athlete in any sport by earnings, and one of the best jockeys of all time.

However, for Cordero, “fame” did not always translate to “beloved.” Known for his flamboyance and cocky attitude, Cordero was a polarizing figure among the public, and although he had many fans, there was a time when bettors in New York loved to hate him. Whether it was due to Cordero’s swagger, or a risky maneuver on the track, or prejudice against Puerto Ricans, or a controversy that threatened to tarnish his career in the 1970s, it was often up in the air if he would be cheered or booed. The public often focused on him if he was in a race, and renowned sportswriter Steve Crist once said of Cordero, “In New York, he is one of the fundamentals of handicapping; thorough bettors consider speed, class, form, pace, track condition, post position, appearance, weight – and Cordero.”

Despite many struggles along his journey to horseracing greatness, Cordero was able to achieve a lot more than most other jockeys thanks to his strong work ethic and his unrelenting drive to succeed. He won the Kentucky Derby in 1974 (Cannonade), 1976 (Bold Forbes), and 1985 (Spend a Buck) on his way to 7,057 total wins. He won two Preakness Stakes (1980, 1984), one Belmont Stakes (1976), and four Breeders’ Cup races. In 1987, Cordero became the fourth jockey to win over 6,000 races. Cordero was inducted into the National Museum of Racing Hall of Fame in 1988 and he won two Eclipse Awards for Outstanding Jockey (1982, 1983). He was also known as the “King of Saratoga” after winning 14 riding titles at the track, including 11 in a row.

Cordero was forced to retire in 1992 when he fell from his horse in a race at Aqueduct and it nearly cost him his life. Even though his spleen was removed due to the accident, he left retirement and saddled up again to ride in the Breeders’ Cup in 1995 against the wishes of his friends and family. He retired again soon after but is still involved with horseracing full-time. Cordero was the agent for fellow Puerto Rican jockey John Velazquez. As of 2021, he is currently based in New York and working with another Puerto Rican jockey, Manuel Franco.

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Chris McCarron is a Hall of Fame jockey from Massachusetts that was renowned for his many major racing wins and his contributions to the racing industry after his retirement. He began racing at 19 years old in 1974 and it was immediately obvious that he had talent: in his first year, he had 547 wins, shattering the previous record set by Sandy Hawley in 1973 for most races won in a year (515).

McCarron would go on to become the first jockey to reach the $200 million earnings mark, as well as earning two Eclipse Awards for Outstanding Jockey, three US Champion Jockey by wins awards, four US Champion Jockey by earnings awards, a Best Jockey Epsy award, a George Woolf Memorial Jockey award, and a Mike Venezia Memorial award. He was also inducted into the US Racing Hall of Fame in 1989. Overall, he won an amazing 21% of all the races he rode, a percentage that has only ever been held by 5 jockeys.

After McCarron retired in 2002, he continued to contribute to preserving and enhancing the horse racing industry. He served as a technical advisor, racing designer, and actor in the 2003 film Seabiscuit. That same year, Magna Entertainment Corporation hired him to serve as Vice President and General Manager of Santa Anita Park. He resigned from the position in 2005 to open the first ever riding academy in the US called the North American Racing Academy.

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Pat Day is an accomplished jockey that is known for both his incredible talent at horseracing and his strong Christian faith. The statue honoring Day at Churchill Downs shows his moment of triumph at the Kentucky Derby in 1992: after winning the memorable race, he raised his hands up towards the sky to praise God. He is known as “Patient Pat” because he was a patient rider that tended to save a horse’s energy for the final stretch, and he would typically not use a horse more than he had to. He was also nicknamed “Baby Hands” by Hall of Fame trainer D. Wayne Lukas.

Day was able to achieve an impressive 8,803 wins over his career, and he retired in 2005 with the fourth most wins of all time and as the all-time leading jockey in money earned. He won the Eclipse Award for Outstanding Jockey four times and was a finalist again in 2001. He was the leading horse jockey in race wins in 1982, 1983, 1984, 1986, 1990, and 1991, and a tough competitor in the big races as well, with five Preakness Stakes wins, three Belmont Stakes wins, and one Kentucky derby win under his belt. He was also a victor of 12 Breeder’s Cups and the inaugural $3 million Breeders’ Cup Classic in 1984.

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Lester Piggott was a famous jockey from England known for his tall stature which earned him the nickname “The Long Fellow”. Although Piggott’s height made it challenging for him to keep his weight down, he was able to ride most of his career at 117 lbs. His family has their roots in horseracing as jockeys and trainers going back to the 18th century, and this early exposure to racing gave him a leg up when he began his racing career at just 10 years old, racing horses his father owned. He was 12 when he won his first official race in 1948.

Piggot amassed a total of 4,493 wins on the Flat in Britain alone and roughly 5,300 wins worldwide over 43 seasons, plus 20 more wins over hurdles. Because of this feat, he is widely acknowledged as one of the greatest flat racing jockeys of all time. Although jockeys Gordon Richards and Pat Eddery had more wins than Piggot overall, with 4,870 and 4,632 wins, respectively, they don’t even come close to Piggott’s record 30 wins in the five prestigious British Classic races. He holds the record for most wins in the Epsom Derby at nine wins, he won the 2,000 Guineas six times, and he was the youngest ever jockey to win the English Triple Crown (2,000 Guineas, Epsom Derby, and St. Leger Stakes) in 1970 aboard the Canadian-bred, Irish-trained colt Nijinsky. No horse has won the English Triple Crown since his triumphant victory. Piggot also won the King George VI and Queen Elizabeth Stakes seven times, the Ascot Gold Cup 11 times, and the Royal Ascot 116 times. In addition to his win record, Piggot left his mark on racing history by introducing and popularizing a new short style of racing where the stirrups were pulled up high.

Piggot was showered in awards and accolades for his incredible accomplishments: he earned the British flat racing Champion Jockey award 11 times (1967, 1968, 1969, 1970, 1971, 1981, 1982), received the Derby Awards, the Cartier Award of Merit, the Sir Peter O’Sullevan Award, Sportsman of the Year, and a BBC Sports Personality of the Year award. He was also awarded the Order of the British Empire (OBE) in 1975, but it was withdrawn in 1988 when he was convicted of tax evasion.

Besides being an excellent jockey, Piggot was a well-known trainer and breeder after he retired from racing in 1985, and he was one of the first jockeys to be offered stallion nominations and lucrative offers to breed their horses. However, his retirement from riding was marred when he was imprisoned for tax evasion in 1987, although he was released after serving one year of a three-year sentence. After his release, he returned to horseracing in 1990. His last win was in October 1994, and he finally retired in 1995. He was inducted into the Racing Post’s Hall of Fame in 2016.

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Laffit A. Pincay, Jr. is a legendary jockey renowned for breaking thoroughbred racing records and being a strong finisher. He was once known as flat racing’s winningest jockey of all time with 9,530 career wins, and he still holds third place in most wins despite retiring two decades ago. Pincay surpassed the previous recordholder, Bill Shoemaker, on December 10th, 1999, with his 8,834th win at Hollywood Park aboard Irish Nip.

As a child, Pincay dreamed of becoming a professional baseball player, but his small stature meant that he would never go pro. His father was a jockey as well, and Pincay learned to ride by visiting the racetracks in Panama and Venezuela and watching his father compete. He began his riding career in his native Panama before drawing the attention of top horseman Fred W. Hooper and agent Camilo Marin, who sponsored him to come to the United States to ride under contract in 1966.

Pincay’s American career started with a bang at Arlington Park in Chicago where he won eight of his first 11 races. He primarily competed in the United States for 39 seasons, including 27 summers at Del Mar, and he became the first jockey to hit 9,000 career wins in the California Cup Distaff at Santa Anita on Chichim for trainer Juan Garcia. His illustrious career includes winning three consecutive Belmont Stakes races and one Kentucky Derby (aboard Swale in 1984), along with five Eclipse Awards for Outstanding Jockey. He was also the United States Champion Jockey by earnings for 7 years.

Pincay retired in April 2003 and remained horse racing’s winningest jockey until Russell Blaze passed Pincay on the all-time win list with over 12,208 wins on December 1, 2006.

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