Celebrated jockeys are part and parcel of horse racing. Measuring their success is very subjective, however. There are various ways of viewing who is the “best” horse jockey ever without resolving the debate.

One measurement for ranking famous horse jockeys is the prize money that they rake in. In addition, you can look at quality and quantity of horse races that they win. Also, there’s career longevity to consider, international success in big horsing events as well as striking up memorable partnerships with famous racehorses. Comparing jockeys from different epochs and places, and with different riding styles, is always challenging.

Being a jockey is a demanding job. Only a handful of individuals will make it to the top. It takes dedication, determination and – of course – talent in order to become the best of the best.

time have made a big name for themselves in the racing world. With wins in the thousands, they have spent their fair share of time in the winner’s circle. Although some of these names may not ring a bell, they are worthy of a place on this list.

Bill Shoemaker

Bill Shoemaker was born on 19 August 1931, in Fabens, Texas. Shoemaker was so small when he was born that his parents were frightened he wouldn’t survive. However, his small size was a massive advantage as a jockey.

Shoemaker’s horse riding career kicked off when he was just a teenager. Quickly he found success in horse racing and within a year of starting his professional career, he was crowned the US Champion Jockey.

Shoemaker bagged the Kentucky Derby four times, the Preakness Stakes twice as well as the Belmont Stakes five times. He netted several other notable races including the Breeders’ Cup, Santa Anita Derby, Hollywood Gold Cup, and Oak Tree Invitational Stakes. He won 8 883 races, which was a record he held for many, many years.

Lester Piggott

Born in 1935 and with well over 4 400 victories to his name, it is difficult to claim that Lester Piggott should not be in our list.  He was tall for a jockey and stood at 5ft 8in. He has many wins to his name including 30 British Classic races, the Prix de l’Arc de Triomphe in addition to the Irish Derby twice.  Piggott won title of British Flat Racing Champion Jockey a massive 11 times.

Laffit Alejandro Pincay Jr.

Born in the mid-1940s in Panama City, Panama, Laffit Alejandro Pincay Jr. was the latest addition to a horse racing family. His father was a jockey as well, riding thoroughbreds on tracks in Panama as well as Venezuela.

At 15, the younger Pincay took up a job as a hotwalker at local tracks. He was thought to be far too big to work as a jockey however he managed to talk the contacts of the thoroughbred Huelen to give him an opportunity. In 1964, long before you could win big with NZ online blackjack casinos, he won his first professional race, riding Huelen at the Hipodromo Presidente Remon situated in Panama City.