In order to become great, a jockey has to have a balance of good management, horse sense, skill, and courage. Others will add perhaps a little aggressiveness and even insanity. Assessing the success of jockeys is extremely subjective. To some, it’s all about the amount of money you rake in. For others, more important is winning the big races, or just winning races on any level.

While the debate about what makes a jockey great goes on, so does the argument of who is the greatest jock of all time. DSport has picked up a list of the top 10 greatest jockeys of all time.

Bill ShoemakerBill Shoemaker

William “Bill” Shoemaker won his first horse race when he was 18. Before retiring 41 years later, he would win 8,882 more. Along the way, he would win basically every major North American race including the Belmont five times, the Kentucky Derby four times, the Preakness twice, and the Breeder’s Cup Classic.

Although the Triple Crown eluded him, his other accolades (among many) include being the United States Champion Jockey by earnings 10 times, by wins five times, winning the George Woolf Memorial Jockey Award, and induction into the National Museum of Racing and Hall of Fame just nine years into his career.

Laffit Pincay Jr.Laffit Pincay Jr.

Laffit Pincay Jr. was once flat racing’s winner all-time jockey, still holding second place many years after his retirement. He competed primarily in the United States. With his 8,834th win, on December 10, 1999, at Hollywood Park Racetrack in California aboard Irish Nip, he broke the career victory record previously held by Bill Shoemaker.

He won the Kentucky Derby and Belmont Stakes in 1984 aboard Swale. Pincay’s win with Swale was his third consecutive Belmont victory, having ridden Conquistador Cielo and Caveat to victory in the previous two years. The four victories in the Triple Crown were the only times Pincay visited the winner’s circle in those races; he never won the Preakness Stakes and failed to win another Triple Crown race after he rode Swale.

At the time of his retirement (in April 2003), he remained most horse racing’s winning jockey, with 9,530 career victories. On December 1, 2006, Russell Baze passed Pincay on the all-time win list. Pincay was inducted into the National Museum of Racing and Hall of Fame in 1975.

Lester PiggottLester Piggott

Lester PiggottLester Piggott

Lester Piggott was already a force in the UK racing scene at the age of 18 when he won the Epsom Derby the first of nine times. Tall for a jockey at 5’8”, he was nicknamed “The Long Fellow” and invented a whole new style of racing that has influenced countless jockeys since.

Always riding under his ‘normal’ weight due to his statute, Piggott would win most of the major European races on multiple occasions, including a total of 30 British Classics races, the Prix de l’Arc de Triomphe and Irish Derby thrice each, and many others.

Eddie ArcaroEddie Arcaro

Even though he is the only jockey to ever ride two different horses to the Triple Crown, Eddie Arcaro is not a name many casual racing fans know. Born prematurely, the Cincinnatian would grow to be just 5’2”, a stature that would ultimately help him win over 24,000 races.

In addition to his historic Triple Crown wins, Arcaro was one of the winningest jockeys of the 1940s and 1950s. He was equally influential off the track, serving as one of the leaders in the formation of the Jockey’s Guild.

Pat Daypat-day

He is a four-time winner of the Eclipse Award for Outstanding Jockey and was inducted into the National Museum of Racing and Hall of Fame in 1991. Day also received the George Woolf Memorial Jockey Award in 1985, given annually to a North American jockey who demonstrates the highest standards of professional and personal conduct.

Day has ridden winners of U.S. Triple Crown races nine times. In 1991, Pat Day won the Canadian Triple Crown and the Breeders’ Cup Distaff aboard the future Hall of Fame filly Dance Smartly. He is the only jockey to have ridden at least one mount in each of the first 20 Breeders’ Cups, and ranks second all-time in Breeders’ Cup winners, with 12.

Kent DesormeauxKent Desormeaux

While many jockeys begin to race at a young age, what Kent Desormeaux accomplished early in his career is nothing short of prodigious. After winning his first graded stakes race at age 16, Desormeaux would go on to win more races than any other jockey in the country. In 1989, his fourth season of regular racing, Desormeaux would set the American single-season record for wins with 597, hauling in more than $9 million that year.

Twice the Louisiana-native would win the first two races in the American Triple Crown, but come up short of winning the Belmont and the honor in 1998 and 2008. He’s also the owner of several Breeder’s Cup victories and is the first foreign jockey to win one of Japan’s Classics races.

Frankie DettoriFrankie Dettori

Frankie Dettori is an Italian horse racing jockey in the United Kingdom. Dettori has been Champion Jockey on three occasions and has ridden the winners of more than 500 Group races. His most celebrated achievement was riding all seven winners on British Champions’ Day at Ascot in 1996. He is the son of the jockey Gianfranco Dettori, who was a prolific winner in Italy. He has been described by Lester Piggott as the best jockey currently riding.

On 11 December 2015 at the Hong Kong Convention and Exhibition Centre Frankie Dettori was named ‘World’s Best Jockey 2015’. He topped ranking with 100 points after five wins, four second-placings, and four thirds.

Russell BazeRussell Baze

There are so many amazing things about the career of Russell Baze. Maybe most notable is that despite being the winningest jockey in North American racing history and racing in over 50,000 races, the dual American-Canadian citizen has never finished higher than 20th on the national earnings list, nor won a Triple Crown race.

This is not to diminish his accomplishments of course. A true grinder if there ever was one, Baze rode (and continues to ride) every race like it was the Triple Crown, no matter the true value. This approach has helped him win 400 or more races in a year, 11 times, something no other jockey has ever done even more than three times. Among Hall of Fame honors and winning the Eclipse Special Award, he has won 13 of the 14 Isaac Murphy Awards ever awarded, given annually to the jockey with the highest winning percentage.

Jorge VelásquezJorge Velásquez

Jorge Velásquez is a thoroughbred horse racing Hall of Fame jockey. In 1967 he won more races than any other American jockey and in 1969 was among the tops in money-winning.

In 1978 he became nationally famous for being one of the jockeys involved in probably the greatest rivalry in racing history. He finished second aboard Alydar to Affirmed in all three of the 1978 American Triple Crown races, losing by a combined total of fewer than two lengths.

Javier Castellano Javier Castellano

Some might argue that Javier Castellano is still too early in his career to have his name placed upon the greats of the sport. But we think that what he has done so in just 20 years of racing is exactly what merits that honor. The Venezuelan won his first major races in 2004, including the Breeder’s Cup Classic aboard Horse of the Year Ghostzapper.

Since then, Castellano has won the Kentucky Derby, Preakness, and numerous other G1 races around the world. From 2013-2015 he was North America’s highest-earning jockey, and his $28 million in winnings is the current single-season record.

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