The Best Horse Jockeys of All Time

Horse racing is known as the sport of kings, and every great king needs a great advisor. Jockeys serve that function in the sport, guiding their horses through each race. A great jockey can make the difference between a champion and a mere contender. Let’s take a look at the five best jockeys of all time. 

David A. Gall

The fourth-winningest jockey of all time, with 7,394 victories, David Gall was inducted into the Canadian Horse Racing Hall of Fame in 1993. Before retiring in 1999, he twice won the most number of North American races in a year: 1979 (479) and 1981 (376). 

The key to Gall’s success? Consistency and volume. Over an astounding 43-year career, he had 41,709 mounts and earned a total of $25 million. This figure was much lower than many of his contemporaries who achieved fewer mounts but participated in higher-profile races.

Gall never raced in the Breeders’ Cup or Triple Crown. He avoided the bigger races, opting to race in smaller ones. Gall made it clear that he preferred to stay away from the spotlight: “In my mid-30s I realized I wasn’t going to make it big. I never joined the rat race because I don’t like rat races. I love horse races.” 

Pat Day

With 40,298 mounts over a career lasting from 1973-2005, Pat Day’s career total was 8,803 victories (a winning percentage of 21.30%). He saw nearly unparalleled success in the Breeders’ Cup and Triple Crown races.

In fact, at retirement, Day was the leading money-winner in Breeders’ Cup history with $23 million over 12 Breeders’ Cups. He won this race in 1984 on Wild Again, 1990 on Unbridled, 1998 on Awesome Again, and 1999 on Cat Thief. The legendary jockey was also successful at the Triple Crown, winning each race at least once:  

  • Kentucky Derby (1992, Lil E. Tee) 
  • Preakness (1985, Tank’s Prospect; 1990, Summer Squall; 1994, Tabasco Cat; 1995, Timber Country; 1996, Louis Quatorze)
  • Belmont (1989, Easy Goer; 1994, Tabasco Cat; 2000, Commendable)  

Bill Shoemaker

Bill Shoemaker’s Encyclopedia Britannic entry calls him “the greatest American jockey of the second half of the 20th century.” His legendary career included many Triple Crown wins in all three events. “Shoe” ran 24 Kentucky Derbies and won four (1955, 1959, 1965, and 1986). He won five Belmont Stakes (1957, 1959, 1962, 1967, and 1975) and two Preaknesses (1963 and 1967). 

During his 41-year career in horse racing, Shoemaker had 8,800 successful mounts. Among North American jockeys, he was the top rider in 1950, 1953, 1954, 1958, and 1959. He was also the top money-winner in a calendar year a whopping 10 times. 

The secret to Shoemaker’s success? “Horses would run for him, and I’ve always wanted to know why,” Hall of Fame jockey Eddie Arcaro told Sports Illustrated. “Shoe got them to run without pushing them. He takes such light hold of a horse that he could probably ride with silk threads for reins.”

Laffit A. Pincay, Jr. 

Active from 1966 to 2003, Laffit Pincay, Jr. led all jockeys in prize winnings seven times (1970-74, 1979 and 1985). When he retired, he’d won a total of over $237 million in prize money. He also retired as the most successful jockey of all time, passing Shoemaker’s record of 8,834 victories. 

Russell Baze 

Pincay’s time as the all-time wins leader was short-lived. Russell Baze surpassed him not long after retiring in 2006. Winning 12,842 career victories, Baze became the first jockey with 10,000 North American victories in 2008. The National Museum of Racing and Hall of Fame sums up his dominance:

Baze led all North American jockeys in wins 13 times (1992, 1993, 1994, 1995, 1996, 2000, 2002, 2005, 2007, 2008, 2009, 2012 and 2014). In 1994, he was voted a Special Eclipse Award for having won 400 or more races in four consecutive years. Overall, Baze had 13 years in which he won 400 or more races, including a career-high of 448 in 1995.