The Kentucky Derby’s most winningest jockeys [Sports]


Still coming off the excitement of longshot horse, I’ll Have Another taking home the Derby crown this year I noted that in NBC’s national broadcast of the event they spoke to several of the jockeys in this year’s race that have won the penultimate horse race several times. While a horse only has one chance to win the Derby there’s no restrictions placed on jockeys, because of that a minority of jockeys have become legends in the city of Louisville. With that in mind, I thought I’d take a look at these individuals who have won the garland on more than one occasion.

The title for the most races won by a single jockey is a tie between Eddie Arcaro and Bill Hartack who each won five races. Arcaro by himself rode in 21 Derby’s from the 1930’s to the 1960’s, his career is one of legend; Winning the annual event in 1938 with Lawrin, 1945 with Hoop Jr., 1948 with Citation, and 1952 with Hill Gail. Probably his most known Derby win came with the famed horse Whirlaway in 1941. Meanwhile, Hartack only actually competed in the Derby twelve times, amazing when you consider he won nearly half. His prime came from the 50’s to the 60’s, winning the Derby initially in 1957 with Iron Leige. Hartack followed that up in 1960 with another victory on Ventian Way; following that in 1962 with Decidedly, 1964 with Northern Dancer, and 1969 with Magestic Prince.  

Just below Arcaro and Hartack, Bill Shoemaker competed in the Derby more times than any other jockey in history- riding in 26 races. During that time Shoemaker won four Derbies, 1955’s on Swaps, 1959’s on Tomy Lee, 1965’s Lucky Debonair, and 1986’s Ferdinand. 

Winning the Bronze medal for most Derbies is a six way tie between Issac Murphy; who’s most famous win arguably came with Buchanan in 1884, Earl Sande whose victory with Gallant Fox in 1930 has the sports press reeling, Angel Cordero Jr. who first won in 1974 with Cannonade, Gary Stevens who’s last Derby victory was in 1997 on Silver Charm, Kent Desormeaux who’s famed ride in 2008 on Big Brown is still discussed, and final Calvin Borel who competed just this year.

Images courtesy of T. Dulay, Getty Images, C.P. Dulay, and

Outside Sources

Kentucky Derby

About Dave Rose
Recently, I completed a Masters degree in Education and have been writing for for over a year now, prior to that I published a humor book for young adults titled Wearing Socks with Sandals, a book about getting through high school, college, and all of the requisite problems that present themselves during that time. Currently, I spend much of my time in classroom settings as well as writing in various areas. Of course, I’m a big sports fan and love music and film, and love finding new stuff around Louisville.
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