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Breeders Cup 2015
Kentucky Derby 2017

Which jockeys have the most Kentucky Derby wins?

KY Derby Jockeys_615x400

To win the Kentucky Derby at least once is part of every jockey's dream, but to win it two, three, four, and even five times really puts a jockey's name in high regard. Featured here are the 10 jockeys with the most Kentucky Derby wins in history, and some of them you can still see riding today.

Bill Hartack (5): Hartack ties the record for the most Kentucky Derby wins. He won with Iron Liege (1957), Venetian Way (1960), Decidedly (1962), Northern Dancer (1964), and Majestic Prince (1969). Decidedly ran the fifth fastest Kentucky Derby and Northern Dancer ran the third fastest.


Eddie Arcaro (5): Arcaro ties with Hartack for winning five times, but two of Arcaro’s mounts were Triple Crown winners, those two horses being Whirlaway (1941) and Citation (1948). Arcaro also won the Kentucky Derby with Lawrin (1938), Hoop Jr. (1945), and Hill Gail (1952). Whirlaway, Citation, and Hill Gail were all owned by Calumet Farm.


Bill Shoemaker (4): Shoemaker’s Kentucky Derby wins came with Swaps (1955), Tommy Lee (1959), Lucky Debonair (1965), and Ferdinand (1986). In 1957, Shoemaker was second with Gallant Man after misjudging the finish line and standing up in his stirrups too soon. He lost to Bill Hartack on Iron Liege that year.


Victor Espinoza (3): Espinoza finally got his Triple Crown victory in 2015 with American Pharoah. He won both the Kentucky Derby and Preakness with War Emblem (2002) and California Chrome (2014), but did not capture the Belmont with them.


Calvin Borel (3): Borel had a lot of success on the Churchill Downs track, including three Kentucky Derby wins with Street Sense (2007), Mine That Bird (2009), and Super Saver (2010). He was the leading jockey at Churchill Downs for four meets.


Kent Desormeaux (3): Desormeaux holds an impressive three-win record for the Kentucky Derby. His first victory came aboard Real Quiet (1998), then Fusaichi Pegasus (2000) and Big Brown (2008). Real Quiet lost the Triple Crown by a nose in a photo finish.


Gary Stevens (3): One of Steven’s best known mounts was Winning Colors, the last filly to win the Kentucky Derby in 1988. Stevens won the 1995 Kentucky Derby and Belmont with Thunder Gulch, and missed the 1997 Triple Crown by 1 3/4 lengths with Silver Charm.


Angel Cordero, Jr. (3): Cordero, Jr. was the jockey of Kentucky Derby winners Cannonade (1974), Bold Forbes (1976), and Spend a Buck (1985). He was born into Thoroughbred racing through his family and stuck with it. Cordero, Jr. now works as a jockey agent.


Earl Sande (3): Sande only had three Kentucky Derby wins, but one of those was Gallant Fox, the 1930 Triple Crown winner. His other winning mounts were Zev (1923) and Flying Ebony (1925). He became a trainer after retiring as a jockey.


Isaac Murphy (3): Murphy is the oldest jockey on this list. He won the Kentucky Derby with Buchanan (1884), Riley (1890), and Kingman (1891). The National Turf Writers Association established the Isaac Murphy Award in 1995 and it is given to the jockey with the highest winning percentage for the year in North America. The winning jockey must ride at least 500 times in that same year.


By Christine Oser


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