Greatest Horse Racing Jockeys
Jockey Laffit Pincay Jr. rides Swale down the home stretch to win the 1984 Kentucky Derby.
Jockeys might be small in stature. On average, they stand about 5 feet and weigh around 100 pounds. But don't let their size fool you.
They are some of the most elite athletes in sports, packing superhuman strength into their small bodies with the instincts to guide 1,000-pound animals around racetracks at 40 miles an hour.
Not all jockeys are created equal, though. The best win thousands of horse races and make hundreds of millions of dollars in career earnings.
These are the greatest jockeys in the history of horse racing.
Note: All statistics are from Equibase and through racing on Oct. 29, 2019.
25. Calvin Borel
Calvin Borel after winning the 2009 Haskell Invitational on Rachel Alexandra at Monmouth Park in Oceanport, New Jersey.
Born: Nov. 7, 1966
Years as jockey: 1983-present (36 years)
Notable horses: Rachel Alexandra, Street Sense, Mine That Bird
Wins: 5,248
Earnings: $132,236,042
Bottom line: Calvin Borel is a Hall of Fame with more than 5,000 career wins, but he’s best known as the rider of three Kentucky Derby winners in a four-year span.
In addition to that trio of high-profile victories, Borel served as the regular pilot of Hall of Fame filly Rachel Alexandra, one of the most beloved thoroughbreds of the 21st century.
24. Russell Baze
Hall of Fame jockey Russell Baze after riding Northland Glory for his 9,998th win at Golden Gate Fields in Albany, California, in 2008.
Born: Aug. 7, 1958
Years as jockey: 1976-2016 (40 years)
Notable horses: Bold Chieftain, Lost in the Fog, Smiling Tiger
Wins: 12,842
Earnings: $199,334,219
Bottom line: North America’s all-time winningest jockey didn’t ply his trade on a major circuit, but on the racetracks of Northern California.
Russell Baze dominated that circuit for the better part of four decades before retiring in 2016 with 12,844 wins, a record that may never be broken.
He was inducted into the Hall of Fame in 1999.
23. George Woolf
George Woolf, far right, with Bold Venture after winning the 1936 Preakness Stakes at Pimlico Race Course in Baltimore, Maryland.
Born: May 31, 1910
Died: Jan. 4, 1946 (age 35)
Years as jockey: 1928-46 (18 years)
Notable horses: Seabiscuit, Kayak II, Challedon
Wins: 721
Earnings: N/A
Bottom line: Immortalized in the movie "Seabiscuit," George Woolf was one of the top riders in the country in the 1930s and 1940s.
Woolf suffered from diabetes, which limited his riding activity, but he was a regular in the winner’s circle following some of the biggest races of the time.
His career was cut short by a fatal accident in 1946.
22. Braulio Baeza
Braulio Baez rides Sherluck to the winner’s circle after the longshot won the 1961 Belmont Stakes.
Born: March 26, 1940
Years as jockey: 1955-76 (21 years)
Notable horses: Buckpasser, Dr. Fager, Ack Ack
Wins: 4,013
Earnings: $36,150,142
Bottom line: One of several top-flight jockeys hailing from Panama, Braulio Baeza came to America in 1960 and was an instant success.
He led all American jockeys in earnings for five straight years, beginning in 1965, and counted Hall of Famers Buckpasser, Dr. Fager and Ack Ack among his regular mounts.
He won two Eclipse Awards for outstanding riding and was inducted into the Hall of Fame in 1976.
21. Ramon Dominguez
Ramon A. Dominguez, aboard Little Mike, celebrates a win in the 2002 Arlington Million at Arlington Park, in Arlington Heights, Illinois.
Born: Nov. 24, 1976
Years as jockey: 1996-2013 (17 years)
Notable horses: Gio Ponti, Better Talk Now, Havre de Grace
Wins: 4,985
Earnings: $191,620,278
Bottom line: Ramon Dominguez established himself as an elite rider on the Mid-Atlantic circuit, where he led all American riders in victories in both 2001 and 2003.
Shortly after that, he moved his track to New York, where he won three straight Eclipse Awards and, in 2012, set a new record for single-season riding earnings.
He retired in 2013 due to injuries suffered in a fall at Aqueduct and was inducted into the Hall of Fame in 2016.
20. Garrett Gomez
Jockey Garrett Gomez, aboard Midnight Lute, after winning the 2008 Breeders' Cup Sprint at Santa Anita Park in Arcadia, California.
Born: Jan 1, 1972
Died: Dec. 14, 2016 (age 44)
Years as jockey: 1988-2015
Notable horses: Blame, Ventura, Midnight Lute
Wins: 3,769
Earnings: $205,224,899
Bottom line: One of horse racing’s ultimate "what might have been" tales, Garrett Gomez was on his way to becoming one of the top riders in the world before serving jail time in the early 2000s.
He came back in 2005 and led all American riders in earnings each year from 2006 to 2009.
However, he relapsed in 2013, officially retired in 2015 and passed away in 2016 from an apparent drug overdose in an Arizona hotel room.
19. Edgar Prado
Edgar Prado rides Benny The Bull to victory in the 2008 Dubai Golden Shaheen, the fourth race of the Dubai World Cup at Nad Al Sheba in Dubai.
Born: June 12, 1967
Years as jockey: 1986-present (33 years)
Notable horses: Barbaro, Benny the Bull, Lemon Drop Kid
Wins: 7,031
Earnings: $269,141,860
Bottom line: A native of Peru, Edgar Edgar Prado dominated the Mid-Atlantic circuit in the 1990s before moving to New York, where he continued to rack up the wins.
He’s won more than 7,000 career races, including the 2006 Kentucky Derby aboard beloved fan favorite Barbaro, and was inducted into racing’s Hall of Fame in 2008.
18. Eddie Delahoussaye
Eddie Delahoussaye in the winner's circle after guiding Sunny's Halo to victory in the 1983 Kentucky Derby at Churchill Downs in Louisville.
Born: Sept. 21, 1951
Years as jockey: 1976-2002 (26 years)
Notable horses: A.P. Indy, Prized, Risen Star
Wins: 6,383
Earnings: $195,809,734
Bottom line: One of many legendary jockeys hailing from Louisiana, the man known as "Eddie D" won two straight renewals of the Kentucky Derby in 1982 and 1983 aboard Gato Del Sol and Sunny’s Halo, respectively.
He also won seven Breeders’ Cup races, and a Grade 3 stakes race at Santa Anita Park is named in his honor.
A winner of 6,383 races, Delahoussaye was inducted into the Hall of Fame in 1993.
17. Kent Desormeaux
Kent Desormeaux riding Big Brown in 2008 after winning the 134th Kentucky Derby.
Born: Feb. 27, 1970
Years as jockey: 1986-present (33 years)
Notable horses: Big Brown, Real Quiet, Summer Bird
Wins: 6,027
Earnings: $285,407,967
Bottom line: The second straight Hall of Fame rider from Cajun Country on this list, Louisiana native Kent Desormeaux has won seven Triple Crown races and six Breeders’ Cup events.
He came close to capturing the Triple Crown with both Real Quiet and Big Brown, and teamed up with brother Keith (a trainer) to achieve great success with Grade 1 winners Texas Red and Exaggerator.
16. Chris McCarron
Chris McCarron, aboard Go For Gin, heads to the winner's circle after winning the 1994 Kentucky Derby.
Born: March 27, 1955
Years as jockey: 1976-2002 (26 years)
Notable horses: Alysheba, Tiznow, John Henry
Wins: 7,141
Earnings: $263,986,005
Bottom line: A legend in California, Chris McCarron was an immediate success upon starting his career, setting a record with 547 winners in 1974 at the tender age of 19.
He was one of the top riders in the world in the 1980s and 1990s, piloting the likes of Hall of Famers John Henry, Alysheba, Sunday Silence, and Tiznow.
He remains one of just two riders to win the Breeders’ Cup Classic five times.
15. Bill Hartack
Bill Hartack, aborad, Majestic Prince, after winning the 1969 Kentucky Derby.
Born: Dec. 9, 1932
Died: Nov. 26, 2007 (age 74)
Years as jockey: 1953-81 (23 years)
Notable horses: Northern Dancer, Majestic Prince, Round Table
Wins: 4,272
Earnings: N/A
Bottom line: A five-time winner of the Kentucky Derby, Bill Hartack remains one of the youngest inductees into racing’s Hall of Fame, having achieved that honor in 1959 at the age of 26.
Perceived as ornery due to frequent clashes with others in racing, he led American riders in victories four times and rode in Hong Kong in the 1970s before officially retiring in 1981.
14. Pat Day
Pat Day, atop Lil E. Tee, after winning 1992 Kentucky Derby.
Born: Oct. 13, 1953
Years as jockey: 1976-2005 (29 years)
Notable horses: Easy Goer, Awesome Again, Cat Thief
Wins: 8,803
Earnings: $297,934,732
Bottom line: Primarily based in the Midwest and New York, Pat Day used a patient riding style to rack up 8,803 career wins prior to his retirement in 2005.
He won nine Triple Crown races (including five renewals of the Preakness Stakes), as well as 12 Breeders’ Cup events, and he led all American jockeys in wins six different times.
13. Gary Stevens
Gary Stevens smiles on Beholder after winning the 2016 Breeders' Cup Distaff at Santa Anita.
Born: March 6, 1963
Years as jockey: 1979-2005, 2013-18 (31 years)
Notable horses: Silver Charm, Beholder, Point Given
Wins: 5,187
Earnings: $258,217,768
Bottom line: Gary Stevens first rose to prominence in the 1980s and remained in the spotlight through various different segments of his racing career.
After being inducted into the Hall of Fame eight years before retiring in 2005, he came back in 2013 to ride the likes of Breeders’ Cup winners Beholder and Mucho Macho Man.
Another retirement came following an accident in late 2018, and he exited the saddle with more than 5,000 career victories.
12. Angel Cordero Jr.
Angel Cordero riding Cannondale after winning the 1974 Kentucky Derby.
Born: Nov. 8, 1942
Years as jockey: 1960-95 (35 years)
Notable horses: Seattle Slew, Slew o’ Gold, Spend a Buck
Wins: 7,057
Earnings: $164,570,627
Bottom line: Aggressive to a fault (ask anyone who watched the 1980 Preakness), Angel Cordero Jr. came to the U.S. from Puerto Rico and rode many of the top horses of his era. This included Hall of Famer Seattle Slew, as well as the winners of six Triple Crown events.
He won 13 riding titles at Saratoga and currently serves as the agent of fellow Hall of Fame jockey John Velazquez (more on him later).
11. Johnny Longden
Johnny Longden seated on Count Fleet in New York in 1943.
Born: Feb. 14, 1907
Died: Feb. 14, 2003 (96 years)
Years as jockey: 1927-66 (39 years)
Notable horses: Count Fleet, George Royal, Busher
Wins: 6,032
Earnings: N/A
Bottom line: Santa Anita Park was Johnny Longden’s personal playground for decades.
He still holds numerous records at the "Great Race Place," and he also swept the Triple Crown in 1943 aboard Hall of Famer Count Fleet.
Longden retired with 6,032 career victories, the last of which came in his final race, when he won the 1966 San Juan Capistrano Handicap atop George Royal.
10. Lester Piggott
Lester Piggott on Never Say Die is led to the winners circle at Epsom, Surrey, in 1954 after winning the Derby.
Born: Nov. 5, 1935
Years as jockey: 1948-95 (47 years)
Notable horses: Nijinsky, Royal Academy, Sir Ivor
Wins: 4,493
Bottom line: The Epsom Derby is England’s answer to the Kentucky Derby. Lester Piggott won the race nine times and earned 11 trophies as Great Britain’s Champion jockey.
He was knighted in 1975, but his honor was stripped following a conviction of tax evasion.
Fittingly, just 10 days after a 1990 return to the saddle, he won a Breeders’ Cup race aboard Mile winner Royal Academy.
9. Javier Castellano
Javier Castellano in the winner's circle after riding Bulletin to victory in the 2018 Breeders' Cup Juvenile Turf Sprint at Churchill Downs.
Born: Oct. 23, 1977
Years as jockey: 1996-present (23 years)
Notable horses: Ghostzapper, Bernardini, City of Light
Wins: 5,198
Earnings: $338,904,353
Bottom line: One of the top jockeys in the country today, Javier Castellano already has built up a Hall of Fame career with plenty of victories still to come.
The 42-year-old native of Venezuela won four consecutive Eclipse Awards from 2013 to 2016 and has finished in the top three in earnings among American jockeys in every season since 2011.
Among his top mounts are Hall of Famer Ghostzapper and champion Bernardini.
8. Gordon Richards
Gordon Richards returns to the paddock after riding a race in 1936 at the Newbury racetrack in England.
Born: May 5, 1904
Died: Nov. 10, 1986 (age 82)
Years as jockey: 1921-54 (33 years)
Notable horses: Nasrullah, Pinza, Tudor Minstrel
Wins: 4,870
Earnings: N/A
Bottom line: Gordon Richards set a standard of brilliance in British racing that jockeys have been trying to reach for more than 60 years.
Over a stretch of 29 seasons, from 1925 to 1953, Richards won Champion Jockey honors an incredible 26 times, and one of the three seasons where he did not hoist the trophy came when he contracted tuberculosis.
He still holds the British record for career victories, having hit the wire first 4,870 times.
7. John Velazquez
John Velazquez pats Wise Dan after winning the 2012 Breeders' Cup Mile at Santa Anita Park.
Born: Nov. 24, 1971
Years as jockey: 1990-present (29 years)
Notable horses: Wise Dan, Ashado, Rags to Riches
Wins: 6,138
Earnings: $413,218,200
Bottom line: A longtime protege of fellow Puerto Rican Angel Cordero, John Velazquez eventually supplanted Cordero as the riding king of Saratoga.
Velazques is the all-time winningest rider at the historic venue, and in addition to that honor, he’s also won 16 Breeders’ Cup races and four Triple Crown events aboard horses like Wise Dan, Ashado, Rags to Riches and Always Dreaming.
6. Jerry Bailey
Jerry Bailey celebrates aboard Sea Hero after winning the 1993 Kentucky Derby.
Born: Aug. 29, 1957
Years as jockey: 1974-2006 (32 years)
Notable horses: Cigar, Skip Away, Empire Maker
Wins: 5,893
Earnings: $296,188,735
Bottom line: Jerry Bailey overcame a battle with alcoholism in the 1980s and emerged on the other side as one of the best riders of his generation.
The 1990s saw Bailey dominate the sport’s biggest races in conjunction with trainers like Bill Mott and Bobby Frankel (among others).
His most notable mount was likely the legendary Cigar, who reeled off 16 consecutive wins from 1994 to 1996.
5. Mike Smith
Mike Smith celebrates with Royal Delta after winning the 2012 Breeders' Cup Ladies' Classic at Santa Anita.
Born: Aug. 10, 1965
Years as jockey: 1982-present (37 years)
Notable horses: Zenyatta, Justify, Holy Bull
Wins: 5,549
Earnings: $326,639,481
Bottom line: One of the most well-known jockeys in the sport, Mike Smith has ridden some of the top thoroughbreds of the past 30 years. In his younger days, he rode horses like Holy Bull and Skip Away.
More recently, he’s known as the primary rider of both beloved Hall of Famer Zenyatta and 2018 Triple Crown winner Justify.
And his success on racing’s biggest days has earned him the nickname "Big Money Mike."
4. Frankie Dettori
Frankie Dettori celebrates aboard Raven's Pass after winning the 2008 Breeders' Cup Classic at Santa Anita Park.
Born: Dec. 15, 1970
Years as jockey: 1985-present (34 years)
Notable horses: Enable, Fantastic Light, Ouija Board
Wins: N/A
Earnings: N/A
Bottom line: Very few jockeys gain mainstream celebrity status, but that’s what Frankie Dettori has earned thanks to success in the saddle and his gregarious personality.
He’s based in Europe, but has had plenty of success in America, where he’s won 14 Breeders’ Cup races.
His "flying dismounts" following wins are highlights, especially given the quality of his mounts, which have included champions such as dual Arc de Triomphe winner Elate.
3. Laffit Pincay, Jr.
Laffit Pincay Jr. with Swale after winning the 1984 Kentucky Derby.
Born: Dec. 29, 1946
Years as jockey: 1966-2003 (37 years)
Notable horses: Affirmed, Swale, Skywalker
Wins: 9,530
Earnings: $237,120,625
Bottom line: Over the course of Laffit Pincay’s career (which spanned more than four decades), the native of Panama racked up 9,530 victories in North America.
This was high enough for him to retire as the winningest jockey in the continent’s racing history.
Along the way, Pincay won seven Breeders’ Cup races and four Triple Crown events, including three straight renewals of the Belmont Stakes in 1982, 1983, and 1984.
2. Bill Shoemaker
Bill "Willie" Shoemaker guides War Allied to the victory circle after winning the first race at Hollywood Park in Inglewood, California, on May 27, 1981.
Born: Aug. 19, 1931
Died: Oct. 12, 2003 (72 years)
Years as jockey: 1949-90 (41 years)
Notable horses: Swaps, Spectacular Bid, Forego
Wins: 8,833
Earnings: $123,375,524
Bottom line: The most dominant rider of the 1950s and 1960s, Bill Shoemaker led American riders in earnings 10 times during his career and piloted the winners of 11 renewals of the prestigious Santa Anita Handicap.
His 11 Triple Crown race wins include the 1986 Kentucky Derby, where the 54-year-old Shoemaker guided longshot Ferdinand through an opening along the inside in one of that race’s most magnificent rides ever.
1. Eddie Arcaro
Eddie Arcaro with Whirlaway after winning the 1941 Belmont Stakes.
Born: Feb. 19, 1916
Died: Nov. 14, 1997 (age 81)
Years as jockey: 1932-62 (30 years)
Notable horses: Citation, Whirlaway, Nashua
Wins: 4,779
Earnings: N/A
Bottom line: Eddie Arcaro was nicknamed "The Master," and for good reason.
He won 17 Triple Crown races during the 1940s and 1950s, and was aboard Triple Crown winners Whirlaway and Citation.
Additionally, he won that era’s biggest race for older horses, the Jockey Club Gold Cup, 10 times aboard legends Nashua, Sword Dancer, and Kelso.