Since 1875, the Kentucky Derby has been held on an annual basis without even a single interruption, which is something that distinguishes it from both the Preakness Stakes and the Belmont Stakes, which are the other two legs of the American Triple Crown. As a result, it should come as no surprise to learn that the Kentucky Derby has seen more than its fair share of legendary horses as well as legendary jockeys.

Here are 5 of the greatest jockeys to ever ride in the Kentucky Derby:

 Eddie Arcaro

Born premature, Eddie Arcaro weighed no more than three pounds at birth. This is something that had life-long consequences for him, seeing as how he never managed to reach more than five foot two inches in height. Something that made him a natural choice for horse racing, as shown by his long list of achievements. For example, he is the jockey who has won the most American classics. Similarly, he was the winner of the U.S. Triple Crown not once but twice, which is something that no other jockey has managed to replicate so far. Given these achievements, it should come as no surprise to learn that Eddie Arcaro also tops the list of Kentucky Derby winners with five wins in 1938, 1941, 1945, 1948, and 1952.

Bill Hartack

While Eddie Arcaro tops the list of Kentucky Derby winners with his 5 wins, it is important to note that he does not share his position alone. The other Kentucky Derby winner with 5 wins is Bill Hartack, who won in 1957, 1960, 1962, 1964, and 1969, while also managing three wins of the Preakness Stakes as well as one win of the Belmon Stakes. Bill Hartack is famous for his contentious relationship with the press as well as some of the other people that surrounded him, though it is interesting to note that he managed to make the cover of Time magazine in 1958 and even co-penned a three-part series about his career in Sports Illustrated.

Bill Shoemaker

For 29 years, Bill Shoemaker held the world record for the most wins as a professional jockey. He started racing horses early in his life, having dropped out of high school to do so and somehow managing to claim the first of his more than 8,800 professional race wins within a month of his debut. Given these results, it should come as no surprise to learn that Bill Shoemaker managed to win the American classics a total of 11 times, though he never managed to claim the coveted U.S. Triple Crown. Furthermore, it should come as no surprise to learn that he is just one win behind both Eddie Arcaro and Bill Hartack with four wins of the Kentucky Derby in 1955, 1959, 1965, and 1986, which gives some indication of the sheer length of his astonishing career.

Isaac Murphy

Having raced in 11 Kentucky Derbies, Issac Murphy managed to win three times in 1884, 1890, and 1891, which was particularly remarkable in that he was a black man who managed to make it in spite of all the factors set against him. Even now, Issac Murphy is remembered as one of the greatest American jockeys ever, not because of his Kentucky Derby wins but because of the fact that he won 628 out of 1,412 horse races, which provides him with a 44 percent victory rate that has never been matched and will probably not be matched anytime soon.

Earl Sande

Like Isaac Murphy, Earl Sande managed to win the Kentucky Derby an impressive total of three times in 1923, 1925, and 1930. Furthermore, it is worth noting that he won the Preakness Stakes three times and the Belmont Stakes one time, as well as numerous other races like all of the other figures mentioned here. After he stopped racing, it is interesting to note that Earl Sande became a horse trainer, which was a natural extension of his lifelong passion for the sport.

Further Considerations

With that said, it is important to note that there have been other legendary winners of the Kentucky Derby as well. For example, while Isaac Murphy and Earl Sande are the only three-time winner to be mentioned here, there are others as well. Moreover, it is important to note that legends are still being made at the Kentucky Derby, meaning that there will always be more to capture the imagination of race watchers.

Nathaniel Berman is Managing Editor of Moneyinc