The Best and Most successful Jockeys of all time

Jockeys in horse racing

Horse racing has been one of the oldest and most popular sports since the dawn of time. The same applies to men, riders or warriors who are skilled and courageous enough to train and ride these strong animals. In the last years, people we call jockeys, and today we’re going to see the most famous jockeys of all time. But first, we’re going to teach you a little bit about the culture and history of horse racing, and then we’re going to get to know the top five famous jockeys.

History & Origin of Horseracing

For understand how and why it began, we’re going back to the distant past, or 4500 BC, when the nomadic tribes domesticated horses for the first time. They were used for both jobs, war and leisure, and when we say leisure, it means races.

If we go a little further in history, we’ll see how horse racing and harness racing were one of the most common games in ancient Greece and the Roman Empire. But the history of our modern horse racing began about the 12th century, when the English crusaders came back with the Arab horses. During the following years, the number of Arab stallions increased, and other English breeds were bred to increase their speed and stamina. Horse racing officially became a formal sport at the beginning of the 18th century. Thanks to this official act, England was overwhelmed with people eager to breed horses. All of this has generated the need for a central authority to be formed in 1750 as the first form of Jockey Club, where the most famous horse jockeys of that time were able to meet and compete.

Man Riding 5 Horses Alone

Furthermore, British emigrants introduced horses and horse racing to America in the same 18th century. It is noteworthy that the first American racetrack was established on Long Island in 1665. Racing as a sport was formally recognised after the Civil War in 1868, but it was followed by an immense expansion, and in 1890 there were 314 horse racetracks throughout the USA. This rapid development introduced the criminal element of racing and the need for a national American Jockey Club, established in 1894 by the largest track and stable owners.

As you can imagine in the 20th century, horse racing was booming in all parts of the world, but in the United Kingdom and the United States, it was much more common than anywhere else. In 1989, there were over 50 million people watching horse racing and over $9 billion worth of wagers were accumulating. It has become very common in Canada, Ireland, the Middle East, South America and Australia. There are many types of races that the people enjoy and they are representative of the 3⁄4 mile run, the 1 1/14 mile race and, of course, the harness race. A lot of riders appeared between 1900 and 2000 and now we’re going to show you the top five most popular jockeys of all time.

Top 5 Most Famous Jockeys

You know how everything began and how sport evolved over the years, but what about our modern era, what about the accomplishments of modern jockeys? Well, now is the time to find out which are the top five most successful jockeys in the history of the sport.


1. Laffit A. Pincay Jr.

Laffit A. Pincay Jr. Jockey

Raised in 1946 in Panama City, Panama, Laffit A. Pincay Jr. started his career as a professional jockey on the Panamanian circuit. The famous breeder Fred W.Hooper took Pincay Jr. under his wing and brought him to the USA, where he showed the world that he was one of the greatest and most famous jockeys of all time.

Following 40 years of cycling, he retired in 2003. Throughout his career, he was able to win almost every major race in the USA, including his 9 victories in the Hollywood Gold Cup. Four more wins in the Belmont Stakes and one in the Kentucky Derby. The sculpture of Laffit A. Pincay Jr. is currently on display in the Santa Anita Park, and its name has also been added to the National Racing Hall of Fame Museum.

2. William `Bill` Shoemaker AKA Bill Shoemaker


This is an emblematic figure in the history of horse racing and is considered to be another famous jockey of all time. It’s not only about his professional success, but also about his inspiring life story. His name was William Lee Shoemaker, but everybody called him Bill Shoemaker. He was born in 1931 with a total weight of 1 kg, and he was never supposed to spend the night, but he did, and on top of that, he survived and lived for almost 70 years.

Bill Shoemaker was a successful jockey not only because of his exceptional skills, but also because he was just 149 cm tall, which certainly helped him produce better racing results. He began pro racing at the age of 18, when he was awarded the United States Champion Jockey in 1950.

It is interesting to note that in his whole career he took this title five times. He moved back to 1990 and wanted to train horses but he was crippled under the neck by a horrific car crash. In 1950 to 1990, he won all three of the Classical American races, the Breeders ‘Cup Classic, The Del Mar Handicap, The Oak Four, The Santa Anita Derby, The Hollywood Gold Cup, and several more.

3. Lester Piggot

Lester Piggott The Jockey

This is another popular legend of jockey but its roots come from the UK. Often known as the long fellow is Lester Piggott because he is 5’8 “or 173 cm, which in contrast with other jockeys is tall. He was born in a horsemen and jockeys family in 1935 and he continued with this tradition. Around 60 years old, he retired from the track, showing a commitment to the sport. Over 100 wins in one season is Lester Piggot’s youngest jockey of his day.

He claimed his first Epsom Derby victory at the age of eighteen. He won the race a total of 9 times in his career, but this is far from all.

Twelve times, he wins the Ascot Gold Cup, the July Cup 10 times, the St. Leger Stakes eight times, the Irish Demby five times, the German Derby three times. He won his last race in 1994 at the age of 59 and retired the following year. The jockey “Oskars,” which has always been one of the most successful jockeys of all time, is named in its honour “Lesters.”

4. Jerry D. Bailey

Jarry D. Bailey The Jockey

Jerry Bailey was born in 1957 and raised in Texas USA. In 1973, when he won Sunland Park Racecourse in New Mexico, he began his career as a professional jockey player. Since then, he won several international competitions such as the Dubai World Cup, the Prince of Wales in 2020, and so on. He won the World Cup in 1996, 1997, 2001, 2002.

He won all American Classic Races and a good number of other Breeders Cup Races on American soil. This is an fascinating reality that jockeys were legal for ads and endorsing products thanks to Jerry Bailey. That’s what happened when he wore advertisements in Kentucky Derby in 2004 on his riding silks. Jerry Bailey formally became part of US Racing Hall of Fame in 1995.

5. Russel Baze

Russell Baze The Jockey

Russell Baze is a name that will always be known by the racing fans because in 2006 he earned a higher score than our first – Laffit Pincay Jr. Russell Baze has more than 10, 000 wins in his career, but the most we have to see is that he still races! At the age of 16, he started his career on the Yakima race track in Washington, Walla Walla. His first victory in 1974 was also won by him.

He was just a child when the horse racing authorities in North America realized how important he is. He was awarded the Eclipse Special Award in 1994 so often in the period from 1992 to 2004.

He was part of the US Racing Hall of Fame back in 1999 and received the George Woolf Memorial Jockey Award in 2002. Between 1995 to 2003 he was honored each year for his excellent jockey achievements, although Ramon Dominguez sadly received the award in 2004. In 2010, Russell Baze won the San Francisco Breeders Club Mile and told the world that he is still one of the greatest and most known horse jockeys ever.