TOP 5: Angel Cordero Jr
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.
TOP 4: Chris McCarron
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.
TOP 3: Patrick Alan “Pat” Day
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.
TOP 2: Lester Keith Piggott
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.
TOP 1: Laffit A. Pincay, Jr.
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.