The Derby-Double Six

February 5, 2023

Isaac Murphy. Photo courtesy of Library of Congress Prints and Photographs Division

By Nick Costa

Beginning with the first Kentucky Derby held in 1875, and including the running of last year’s edition, there have been 1,977 horses contest the springtime classic piloted by 698 individual jockeys. Although Eddie Arcaro and Bill Hartack are tied with the most Derby wins (5), neither jockey had ever ridden back-to-back winners in the annual event for three-year-old horses. However, six jockeys HAVE turned the trick of booting home winners in consecutive years. Incidentally, all six are enshrined in the National Museum of Racing and Hall of Fame.

Isaac Murphy – 1890, 1891

Black jockeys dominated the sport of Thoroughbred horse racing in its early years, from the onset of the first Derby until shortly after the turn of the 20th century. Isaac Murphy was the greatest African American jockey in history. Born in 1861 in Frankfort, Kentucky, Murphy rode from 1876-1895, riding in eleven Kentucky Derbies, and became the first jockey to win the race three times. His first win was aboard Buchanan in 1884, and then he rode Riley to victory in 1890 and Kingman the following year, thus becoming the first rider to win the Derby consecutively. He retired with 530 wins from 1,538 mounts, a phenomenal 34-percent win rate. An award bearing his name is given out to the jockey with the highest winning percentage in North American racing. Murphy died in 1896 and was buried in an unmarked grave. His remains were subsequently found and exhumed in 1967 from their original burial location and moved to a plot at the Kentucky Horse Park in Lexington where he is interred next to the legendary Man O’ War. Hall of Fame Induction 1955

Jimmy Winkfield – 1900, 1901

Jimmy Winkfield. (Courtesy of Keeneland Library Cook Collection)

Another Kentucky native, Jimmy Winkfield hailed from Chilesburg, and rode in the Kentucky Derby four consecutive years. Winkfield finished third on his first Derby mount in 1900 and then he won back-to-back aboard His Eminence in 1901 and Alan-a-Dale in 1902. The following year, Winkfield just missed winning an unprecedented three in a row when his horse led in deep stretch before finishing second. He was the last black jockey to win the Kentucky Derby. In 1904, Winkfield went overseas to ride and was Russia’s champion jockey three times. He also rode successfully in Germany. When he retired from riding at age 50, Winkfield had amassed over 2500 wins in various countries during his 30-year riding career. He died in France in 1974 at age 92. A race named in his honor by the NYRA is contested each year at Aqueduct. Hall of Fame Induction 2004

Ron Turcotte – 1972, 1973

A pensive Ron Turcotte and a very perky Secretariat in the post parade before the 1973 Preakness Stakes at Pimlico Race Course. (Jim McCue/Maryland Jockey Club)

Seven decades passed before the next back-to-back Derby-winning feat would be performed again. This time it was a Canadian-born rider who hailed from New Brunswick, Canada. Ron Turcotte, or “Ronnie” as he was often called, captured the Kentucky Derby in 1972 with Riva Ridge, and the Belmont Stakes, then the following year he became internationally famous when he piloted the immortal Secretariat to a Triple Crown sweep, setting records in each of the three races, becoming the first horse since 1948 to achieve the accomplishment. As a young rider, his stock began to rise in 1965 when Tom Rolfe became his first classic mount. Not only did the horse finish in the money in all three spring classics with Turcotte aboard, but he also captured the Preakness Stakes. While riding in the U.S., Turcotte began working with fellow Canadian, Lucius Laurien, who would go on to condition both Riva Ridge and Secretariat. The brilliant jockey, who had a total of five Derby mounts, piloted home 3,032 winners before his riding career ended tragically after a horrific injury in 1978. Turcotte is also a Hall of Fame member in his native land. Hall of Fame Induction 1979

Eddie Delahoussaye – 1981, 1982

Eddie Delahoussaye (Courtesy of Cindy Pierson Dulay/

In the 1981 Kentucky Derby, Eddie Delahoussaye rallied his horse, Woodchopper, from 21 lengths back only to fall short by three-quarters of a length at the end of the mile-and-a-quarter classic. The following year, Delahoussaye timed his ride perfectly, bringing Gato Del Sol, a 21-1 longshot, from 19th and last place at the half-mile pole to finish first under the wire to claim the roses, then struck again in 1983 when guiding Sunny’s Halo home to become the fourth jockey to win consecutive editions. He rode in the Kentucky Derby 13 times. The Louisiana-born Delahoussaye registered his first win in 1968 and when he retired 34 years later, he had made 6,384 trips to the winner’s circle. Delahoussaye won more than sixty major races in his career, including five Triple Crown races and a total of seven Breeders’ Cup races. Hall of Fame Induction 1993

Calvin Borel – 2009, 2010

Calvin Borel signing a racing form after a race at Churchill Downs (Joe Schneid, Louisville, Kentucky/Wikipedia Creative Commons*)

When it comes to jockeys from Louisiana, lightning does strike twice in the same place. That place was Churchill Downs, and the lightning bolt was Calvin Borel, who, like fellow rider Eddie Delahoussaye, hails from the Pelican State, and struck for back-to-back Derby glory, bringing home a memorable and shocking 50-1 longshot Mine That Bird in the slop in 2009, and Super Saver, the next year, also in the slop. Those victories were Derby wins two and three for Borel, who notched his first Derby score in 2007 aboard Street Sense. Borel was the first and only jockey to amass three Derby wins within a four-year period. Borel had a total of twelve mounts in the Kentucky Derby and rode in the race consecutively from 2007 until 2014. Although he retired from racing in 2016, Borel wasn’t particularly fond of retirement, and he was back riding six months later. His total number of wins through 2022 stood at 5,275. Hall of Fame Induction 2013

Victor Espinoza – 2014, 2015

Victor Espinoza after winning the G2 Princess Rooney aboard Ce Ce at Gulfstream Park July 2, 2022. (Coglianese Photos)

The first opportunity to ride in the Kentucky Derby for Victor Espinoza presented itself in 2001 and the native of Mexico did well and finished third. The next year, Espinoza rode War Emblem to win the Kentucky Derby. Then, after a trio of uninspiring Derby finishes, Espinoza got back to the Kentucky Derby winner’s circle in successive years. First with California Chrome in 2014 and aboard American Pharoah the very next year. All three of Espinoza’s Derby winners had the chance to become America’s 12th Triple Crown winner, but War Emblem and California Chrome were denied in the final leg. However, the third time turned out to be the charm for Espinoza as American Pharoah got the elusive Belmont win, finally putting an end to the Triple Crown drought which American racing fans had endured for 37 years. Espinoza rode in 10 Kentucky Derbies, with his last Derby ride coming in 2018. The seven-time classic-winning pilot is still actively riding and through 2022 he had accumulated 3,494 wins. Hall of Fame Induction 2017

*This file is licensed under the Creative Commons Attribution 3.0 Unported license.

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