The Most Famous Jockeys of All Time

Horse racing is one of the oldest and most respected sports since the beginning of time. The same applies to the people, the riders or the warriors who are skillful and brave enough to train and ride these powerful animals. In the last centuries such people we call jockeys and today we will overview the most famous jockeys of all time. But first, we intend to tell you a bit more about the culture and history of horseracing and then to familiarize you with the top 5 famous jockeys.
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History & Origin of Horseracing

To understand how and when it started, we will go way back in the distant past or 4500 BC when the nomadic tribes domesticated horses for the first time. They were used for both work, war and fun, and when we say fun, that means races.

If we go a bit further in history, we will see how horse racing and harness racing were one of the most popular games in ancient Greece and the Roman Empire. But the origins of our modern horse racing started around the 12th century while English crusaders were coming back with Arab horses. In the following centuries, the number of Arab stallions increased, and they were bred with other English breeds to increase their speed and endurance. At the beginning of the 18th century horse racing officially became a professional sport. Thanks to this official act, England was flooded with people willing to breed racehorses. All of that created the need of a central authority which was established 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

Meanwhile, in the same 18th century, British emigrants brought horses and horse racing to America. It is an interesting fact that the first American racetrack was built in 1665 on Long Island. Racing as a sport was recognized officially after the Civil War in 1868, but it was followed by an enormously big expansion, in 1890 there were 314 horse racetracks across the USA. This rapid growth brought the criminal aspect to the racings and the need of a national American Jockey Club, which was founded in 1894 by the biggest track and stable owners.

As you can imagine in the 20th century, horse racing was flourishing in all parts of the world but in the UK and the USA, it was way more popular than anywhere else. In 1989 there were over 50 million people who attended horse racings and it accumulated over $9 billion wagers. It became super popular in Canada, Ireland, the Middle East, South America and Australia. There are several types of races that the public adore and those are the typical ¾ of a mile race, the 1 1/14 mile race and of course the harness racing. Many riders emerged in the period between 1900-2000 and now we intend to show you the top 5 most famous jockeys of all time.

Top 5 Most Famous Jockeys

You know already how everything started and how the sport was developed through the centuries but what about our modern world, what about the achievements of the modern jockeys? Well, now is the time to find out which are the top 5 most famous jockeys in the history of the sport.

1. Laffit A. Pincay Jr.

Laffit A. Pincay Jr. Jockey

Born 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 is one of the best and most famous jockeys of all time.

He retired in 2003 after 40 years of racing. During his career he was able to win almost every major race in the USA including his 9 wins on the Hollywood Gold Cup. Three other wins in the Belmont Stakes and one in the Kentucky Derby. A Laffit A. Pincay Jr. sculpture is currently exhibited at the Santa Anita Park, also his name was added into the National Museum of Racing Hall of Fame.

As a token of appreciation for his dedication to the sport, each year he is awarded as an important member of the racing community on the Hollywood Gold Cup Day.

2. William `Bill` Shoemaker AKA Bill Shoemaker

William-AKA-Bill-Shoemaker-Jockey

This is an emblematic figure in the horse racing history and considered as another famous jockey of all times. It’s not only about his professional achievements but also 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 1kg and it was never expected from him to pass the night, but he did and on top of that, he survived and lived almost 70 years.

Bill Shoemaker became a famous jockey not only because of his amazing skills but also because he was only 149cm tall, which undoubtedly helped him achieve better racing results. He started pro racing at the age of 18, while in 1950 he was awarded as the United States Champion Jockey.

It’s interesting to mention that he took this title 5 times in his whole career. In 1990 he retired and decided to train horses but a tragical car accident left him paralyzed below the neck. In the period between 1950 and 1990 of his active career, he won all three of the Classical US races, the 1987 Breeders’ Cup Classic, The Del Mar Handicap, The Oak Three Invitational Handicap, The Santa Anita Derby, The Hollywood Gold Cup and many more.

3. Lester Piggot

Lester Piggott The Jockey

This is another most famous jockey legend, but his origin comes from the United Kingdom. Lester Piggott is also known with his nickname “the long fellow” because he is 5`8“ or 173cm which is respectively tall compared with other jockeys. He was born in 1935 in a family of horseman and jockeys and he continued that legacy. He retired from the track around the age of 60, which shows his dedication and passion for the sport itself. Lester Piggot became the youngest jockey of his time with over 100 wins in a single season.

At the age of 18, he scored his first victory in the Epsom Derby. Indeed, in his whole career, he won that race in total 9 times, but that is far from all.

He won the Ascot Gold Cup eleven times, the July Cup 10 times, the St. Leger Stakes 8 times, the Irish Derby 5 times, the German Derby 3 times, he even won the Singapore Derby. In 1994 at the age of 59, he won his last race and retired the next year. The jockey “Oskars” was named in his honour “Lesters”, up to this date Lester Piggot is still one of the most famous jockeys of all time.

4. Jerry D. Bailey

Jarry D. Bailey The Jockey

Born in 1957 and raised in Texas USA, Jerry Bailey started his career as a professional jockey in 1974 when he won the Sunland Park Racecourse in New Mexico. From then on, he conquered many international circuits like the Dubai World Cup (1996, 1997, 2001, 2002), The Prince of Wales`s Stakes in 2020 and more.

On American soil, he won all American Classic Races and many other Breeders Cup Races. It is an interesting fact that thanks to Jerry Bailey, jockeys were legally allowed to advertise and promote brands. That happened after he wore advertising patches on his riding silks in Kentucky Derby 2004. In 1995 Jerry Bailey became officially part of the United States Racing Hall of Fame.

He also got the Eclipse Award for Outstanding Jockey not once, but 7 times in his whole life. He won the George Woolf Memorial Jockey Award too in 1992 and he continues the passion of his life – horse racing but as an ESPN commentator.

5. Russel Baze

Russell Baze The Jockey

Russell Baze is a name that the racing fans will always remember because in 2006 he achieved a bigger winning score than our top 1 – Laffit Pincay Jr. Over his whole career Russell Baze has over 10,000 wins, but the best we are yet to see because he is still racing! His career started at the age of 16 while he was riding at the Yakima Racetrack in Walla Walla, Washington, also where he got his first win in 1974.

His talent was spotted while he was only a teenager when the North American horse racing authorities saw how valuable he is. Between 1992 and 2004 he was awarded so many times, Eclipse Special Award in 1994.

In 1999 he was already part of the United States Racing Hall of Fame, in 2002 he won the George Woolf Memorial Jockey Award. Between 1995 and 2003, each year he was awarded for outstanding jockeying achievement, unfortunately, in 2004 the award was taken by Ramon Dominguez. In 2010 Russell Baze won the San Francisco Breeders Club Mile and showed the world that he is still on track and still one of the best and most famous horse jockeys of all time.

Hope you enjoyed our article! If you are looking for more interesting information regarding horses and horse races you should read The Greatest Racehorses of All Time and the Charity Race Night. Both articles will show you some additional information and things that you probably don’t know about horse racing. In case you are bored, and you are looking for some fun, consider checking the best sports betting sites, where you can bet on horse racing and back the current best jockeys. Or maybe you can visit some of the top 10 online casinos in the world and enjoy other types of gambling. In any case, you’ll have a good time!

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