Greatest Horse Racing Jockeys

Jockey Laffit Pincay Jr. rides Swale down the home stretch to win the 1984 Kentucky Derby. AP Photo
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

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

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

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

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.