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Success in horse racing is a combined effort, with the raw power of a champion horse supported by a team made up of owners, trainers and those diminutive strategists from the saddle, the jockeys.
Jockeys blend courage with intelligence to guide their steed through what can be a uniquely chaotic environment at the track, and the best ones are rightly celebrated.
In terms of notoriety, a select few stand out from the rest, not just for their huge tallies of victories, but for the indelible mark they’ve left on the sport as a whole. Below, we’ve ranked our top five greatest jockeys ever.
5. Frankie Dettori: The Flamboyant Maestro
Born in the fashionable city of Milan in 1970, Frankie Dettori exploded onto the racing scene like a shooting star, with his unique brand of showmanship. His career, which spanned over three decades, spawned north of 3,000 victories.
Among those were over 250 Group 1 triumphs, with wins in the UK, France, Qatar, Germany, Hong Kong and beyond, a testament to his versatility across continents.
Dettori’s flair wasn’t just for the cameras, however. He wove it into his riding style, where his bold tactics and bravery delivered some of the sport’s most unforgettable moments.
His “Magnificent Seven” at Royal Ascot in 1996, a feat that is unlikely to be repeated, saw Dettori win all seven races on the card for his connections at Godolphin – an effort he would call his “greatest sporting achievement”.
Dettori’s flying dismounts from his rides have provided reams of iconic footage, while his charisma has made him a cult hero with racing fans.
At 54, Dettori is still competing, having u-turned on a decision to retire in 2023, and punters are still backing him on horse racing betting sites today. However, nothing lasts forever, so enjoy him while you still can.
4. Sir Gordon Richards: The Unyielding Champion
In the annals of British flat racing, Sir Gordon Richards still reigns as one of the greatest ever to do it and a certified colossus of consistency.
Born in Shropshire in 1904, Richards was in the saddle by 13 and quickly rose to dominance thereafter. When he finally retired in 1954, he had amassed more than 4,800 wins, a record that proved unbeatable for decades.
Knighted in 1953, Richards remains the only flat jockey to receive such an honour, though the accolade was thoroughly deserved after his mammoth haul of 26 British Champion jockey titles in 29 seasons.
A pioneer of positioning techniques, Richards was a trailblazer and innovator, and among this bounty were 14 British Classics.
Off the track, his transition to training kept him in the fold, with family members carrying the torch today, ensuring his legacy in the sport endures.
3. Laffit Pincay Jr.: The Relentless Record-Breaker
From the other side of the pond, we have Laffit Pincay Jr, a jockey from Panama City who achieved the American dream in spectacular style.
Born in 1946, Pincay lodged more than 9,500 wins across his 37-year career, making him North America’s most successful jockey of all time, until he was recently surpassed.
With over $237 million in prize money banked, Pincay was a money-making machine for his connections stateside.
Perhaps his pinnacle came in 1978 when he rode Affirmed to the Triple Crown (the Kentucky Derby, Preakness Stakes and Belmont Stakes), boosting his seven Breeders’ Cups and four Kentucky Derby overall wins.
Pincay was still competing as recently as 2003, before a leg injury forced him into retirement, though he left the sport with his legendary status enshrined.
2. Bill Shoemaker: The Shoe That Fits Perfection
Wille “The Shoe” Shoemaker was a Texan giant of a featherweight, who was responsible for more than 8,800 wins over 41 years, amassing north of $120m in prize money, before his transition to trainer.
A Hall of Fame inductee, Shoemaker won four Kentucky Derbies, five Belmont Stakes and five Preakness races, a collection that puts him on a pedestal in American racing circles.
In 1986, at the ripe age of 54, Shoemaker became the oldest-ever winner of the Breeders’ Cup with the help of Ferdinand, an outstanding testament to his skill and longevity.
Leading U.S. earnings 10 times, he won the Santa Anita Handicap 11 times and mentored countless riders along the way. Tragically, he passed in 2003, though his memory lives on. There is a wonderful bronze statue of Shoemaker atop Kentucky Derby winner Swaps at Hollywood Park.
1. Lester Piggott: The Long Fellow’s Enduring Reign
At the summit of our list of the greatest jockeys ever sits Lester Piggott and few racing fans would argue against his position at the top.
Born in 1935 into a jockey’s bloodline, the enigmatic Englishman carried the torch from his grandfather, who himself was a Derby winner in 1919.
Piggot was following in his footsteps from the age of 12 and clocked 4,400+ wins during his incredible career. Over five decades, he won 30 British Classics, including nine Epsom Derbies.
His 1970 Triple Crown success aboard Nijinsky is still fondly and vividly remembered today, while his 11 Champion Jockey titles and 116 Royal Ascot wins only add to his mythical reputation.
Nicknamed “the Long Fellow”, with his 5’8” height making him tall among jockeys, Pigott’s lean-forward style signature stance was easy to pick out and just as easy to back in the betting markets.
Retiring in 1995, he influenced sons and grandsons in the saddle, while statues at Epsom and Ascot pay eternal tribute to the greatest jockey to ever take the reins.
