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Top Five Throwback Kentucky Derby Jockeys

Top Five Throwback Kentucky Derby Jockeys: As the first Saturday in May approaches its eagerly awaiting devotees, it is important to reflect on the historical importance of the Kentucky Derby. Owners and breeders and the horses themselves take up much of the spotlight for the big race, but jockeys also deserve a significant amount of attention. Here’s a brief history of some of the most successful riders in bygone editions of the iconic Kentucky Derby.

Top Five Throwback Kentucky Derby Jockeys

Actress Jayne Mansfield with jockeys Johnny Longden, Eddie Arcaro and Willie Shoemaker.
Photo: fold3.com

Eddie Arcaro
One of two jockeys to score an otherwise unprecedented record of five victories in the Kentucky Derby, Eddie Arcaro won more American classic races than any other jockey in history and is largely considered to be the best jockey the United States has ever produced. Old “Banana Nose,” a nickname awarded to him by his cohorts due to his relatively large nose, was born prematurely into a poor family of Italian immigrants, a circumstance that plagued him with small size during his younger years. His eventual growth to a mere 5’2” may have seemed rather disadvantageous at the time, but nothing could have been more of a blessing for the racing world. Arcaro began racing at age sixteen at the Agua Caliente racetrack in Tijuana in 1932, and while still largely under the shadow of anonymity, he was given his first mount in the 1938 Kentucky Derby aboard Lawrin and his first Kentucky Derby trophy as he drove his mount down the track to victory. The young Arcaro rose to prominence and dominated the ranks of jockeys, winning four more editions of the Kentucky Derby. Two of his wins came aboard Triple Crown winners Whirlaway (1941) and Citation (1948), whereas in the other two he partnered with Hoop Jr. (1945) and Hill Gail (1952) on his way to five total victories in the “Run for the Roses.” Eddie Arcaro was justly elected to the Hall of Fame in 1958, and the memory of “the Master” persists as current jockeys continue to idolize his expert and unmatched riding skills.

Bill Hartack
Sharing the top record of five Kentucky Derby victories is Bill Hartack, the son of a Pennsylvania farmer. At age seventeen Hartack maxed out at 5’4” and weighed only 111 pounds, making him the perfect size to become the next great jockey. He began racing in 1953 and managed to achieve the status as a prominent jockey quite quickly, becoming the United States’ leading jockey in only his third season and going on to be awarded that recognition three more times during his career. His first Kentucky Derby victory came about quickly as well when he guided Iron Liege to the finish line in 1957. Hartack reeled off his four other Derby winners rather consistently, winning with Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), and Majestic Prince (1969). Unfortunately, Hartack missed out on what could have been his sixth Kentucky Derby victory aboard eventual winner Tim Tam when he broke his leg two weeks before the 1958 running of the race and was unable to ride. The skillful jockey was featured on the cover of Sports Illustrated twice during his career, and he even made the cover of Time in 1958. Bill Hartack was inducted into the Hall of Fame at the young age of 27, and following his retirement from riding, he worked as a steward for various racetracks around the country.

Top Five Throwback Kentucky Derby Jockeys

Jockey superstar Bill Shoemaker signs autographs for the crowd after he rallied Glamour Betty to win the feature race at Playfair in 1987. Photo: spokesman.com

Bill Shoemaker
The Texas-born William Shoemaker, or simply “Bill,” “Willie,” or “The Shoe,” achieved four Kentucky Derby victories during his days of racing. Much like Arcaro, Shoemaker was born prematurely and remained small his whole life, growing to only 4’11” and weighing 105 pounds. While he was certainly considered to be small in the regular world, in the racing world he became a celebrated giant. After dropping out of high school, Shoemaker began racing in 1949 at age eighteen, and by 1955 he had his first mount in the Derby aboard Swaps. Shoemaker’s next Derby victories came a few years later aboard Tomy Lee (1959) and Lucky Debonair (1965), and with his win aboard Ferdinand in 1986, he became the oldest jockey to ever win the race at the age of 54. “The Shoe” would have likely stolen a victory from Hartack and racked up five Kentucky Derby victories with the addition of the 1957 Derby, but he misjudged the finish line while riding Gallant Man and allowed Iron Liege and Hartack to sneak by them for the win. Regardless of his mistake, Shoemaker certainly managed a lifetime full of accomplishments, including 8,833 race wins and victories aboard such great horses as Forego, Buckpasser, Damascus, John Henry, Spectacular Bid, and Silky Sullivan.

Isaac Murphy
No list of great American Thoroughbred jockeys is complete without the inclusion of Isaac Murphy. The African American legend was born and initially named Isaac Burns in Frankfort, Kentucky, at the start of the tumultuous Civil War 1861, but after his father’s death, the family moved to Lexington to live with his grandfather, Green Murphy. When Isaac became a jockey at the young age of 14, he changed his last name to Murphy in honor of his beloved grandfather. In conjunction with multiple other jockeys, Murphy was able to collect three Kentucky Derby wins in eleven attempts in the race. His first victory came aboard Buchanan in 1884, and he then won atop Riley in 1890 and Kingman in 1891. Significantly enough, Kingman became the only horse owned by an African American to win the Kentucky Derby. While his racing record remains largely incomplete, Murphy is credited with 530 wins in 1,538 starts, forming a remarkable win rate of 34%. In recognition of his prowess, fellow great jockey Eddie Arcaro claimed, “There is no chance that his record of winning will ever be surpassed,” and upon the creation of the National Museum of Racing and Hall of Fame, Murphy was the first jockey to be inducted. The great jockey of the American turf is rightfully buried alongside Man o’ War at the entrance of the Kentucky Horse Park, and the memory of his greatness continues to inspire current jockeys.

Earl Sande
Another bygone winner of three editions of the Kentucky Derby is Earl Sande. Sande was born at the close of the 19th century in South Dakota, and in his early days he first worked with horses as a bronco buster. The eventual champion Thoroughbred jockey then switched to riding quarter horses before finding his way to the racetrack in 1918. It only took five years before he won his first blanket of roses aboard Zev in 1923, and in 1925 he won his second Derby on Flying Ebony. His ultimate accomplishment came in 1930 when he was awarded the successful Kentucky Derby mount on the great Gallant Fox and then guided that colt to victories in both the Preakness and the Belmont, thus becoming the second Triple Crown winner in American history. Earl Sande retired as a jockey in 1932, and while his riding career was rather short-lived, he remained involved in the industry as a trainer. Sande’s feats during his career caught the attention of the poet Damon Runyon who made the jockey the focus of many of his pieces, and he was inducted into the Hall of Fame in 1955. Regardless of his brief career as a jockey, Sande swept in like a whirlwind and claimed multiple prominent races to forever stamp his name as one of the all-time greats.

While these five jockeys of the past are of utmost importance in the history of racing, it is important to note that many contemporary jockeys are on the threshold of Kentucky Derby greatness as well. Gary Stevens, Kent Desormeaux, and Calvin Borel each have three victories in the American classic, and they, among others, could each easily attain the heights of past renowned jockeys.

Related Links:
Top Five Kentucky Derby Upsets of All Time
Top Five Kentucky Derby Trainers of All Time
Kentucky Derby Travel Tips: Top Five Churchill Downs Photo Ops
Kentucky Derby Travel Tips: Top Five Farms to Visit

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