Preakness History: Jockeys With Most Wins In Second Leg of Horse Racing’s Triple Crown

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Written By Giovanni Shorter | Last Updated
Preakness Stakes Jockeys Wins

The second leg of horse racing’s Triple Crown, the Preakness Stakes, is scheduled annually to run two weeks after the Kentucky Derby. The jockey can be an important element when factoring in how to bet on Preakness odds. Among past winners, two jockeys have separated themselves from the rest for the most all-time wins in Preakness history.

Eddie Arcaro – Six Wins (1941, 1948, 1950, 1951, 1955, 1957)

(AP Photo/John Rooney)

The jockey with the most wins in Preakness history is Eddie Arcaro. Arcaro won the Preakness Stakes six times. In addition, Arcaro also holds the record for most Triple Crown race wins, with five Kentucky Derbies and six Belmont Stakes under his belt. Arcaro is the only jockey to win the Triple Crown twice.

Pat Day – Five Wins (1985, 1990, 1994, 1995, 1996)

(AP Photo/Jim McKnight)

Pat Day has the second-most wins in Preakness history, taking the honor five times. When he retired in 2005, Day finished with 8,803 career wins, which ranked him fourth all-time. He also finished as the all-time leading jockey in money earned.

Day has won nine Triple Crown races and 12 Breeder’s Cup mounts. Day also has ten second-place finishes and four third-place finishes in American classic races.

Multiple Jockeys – Three Preakness Wins

Victor Espinoza

(AP Photo/Jae C. Hong)

Victor Espinoza won the Preakness Stakes in 2002, 2014, and 2015. Espinoza also won the Kentucky Derby in the same three years. He managed to win the Triple Crown in 2015 with American Pharoah and is the first jockey to enter the Belmont Stakes with a chance to win the Triple Crown on three occasions. Espinoza is still riding today.

Bill Hartack

preakness history
(AP Photo)

Bill Hartack won the Preakness Stakes in 1956, 1964, and 1969. He is also one of two jockeys (the other being Eddie Arcaro) to be a five-time Kentucky Derby winner. In 1964 and 1969, he won both the Kentucky Derby and Preakness Stakes but did not manage to win the Triple Crown in his career. He did manage to win the Belmont Stakes once in 1960.

Hartack was inducted into the National Museum of Racing and Hall of Fame in 1959 at 26 years old.

George Barbee

George Barbee won the first-ever Preakness Stakes in 1873 and managed to win by ten lengths. This was the record until Smarty Jones broke it in 2004. Barbee also won the Preakness in 1876 and 1883. His three Preakness Stakes wins were the record for most wins until Eddie Arcaro won his fourth in 1951. Barbee holds one other American classic race win with the 1874 Belmont Stakes.

He was inducted into the Hall of Fame in 1996.

Lloyd Hughes

Lloyd Hughes won the Preakness Stakes in 1875, 1879, and 1880. He also won the Belmont Stakes twice, the Travers Stakes twice, and the Dixie Handicap four times. Hughes was actually the first jockey to win the Preakness three times, as he won his third in 1880, and Barbee had not won his third until 1883.

Hughes is also the first jockey to win the Dixie Handicap four times and the only one to win it four consecutive times.

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