The 37 Most Legendary Kentucky Derby Winners of All Time

The Kentucky Derby has been run since 1875, producing legendary champions who captured hearts worldwide. Which Derby winner is the greatest racehorse in the history of the Run for the Roses?

1. 1
   Secretariat

   The greatest racehorse in history who set the still-standing 1973 Derby record of 1:59 2/5 en route to the Triple Crown.
   1000pts
2. 2
   Donerail

   At odds of 91-1, Donerail won the 1913 Derby in record time and remains the longest-priced winner in the race's history.
   882pts
3. 3
   Zev

   Zev won the 1923 Derby and Belmont, then beat English Derby winner Papyrus in a $100,000 match race at Belmont Park.
   882pts
4. 4
   Sir Barton

   The very first Triple Crown winner in 1919, though the concept was not formally recognized for another decade.
   802pts
5. 5
   Northern Dancer

   The 1964 Derby winner who became the most influential sire in modern Thoroughbred history, reshaping racing forever.
   778pts
6. 6
   Gallant Fox

   Earl Sande rode him to the 1930 Triple Crown, and he later sired Omaha, making them the only father and son who both won it.
   694pts
7. 7
   War Admiral

   A powerful 1937 Triple Crown champion immortalized by his legendary match race defeat against Seabiscuit.
   694pts
8. 8
   Citation

   Calumet Farm's 1948 Triple Crown winner under Eddie Arcaro won 16 races in a row and became the first racehorse to earn $1 million.
   694pts
9. 9
   Alysheba

   Alysheba nearly fell after clipping heels in the 1987 Derby stretch but recovered to win, and later retired as the world's richest racehorse.
   694pts
10. 10
    Aristides

    Aristides won the first Kentucky Derby in 1875, ridden by Black jockey Oliver Lewis and trained by Black horseman Ansel Williamson.
    629pts
11. 11
    Big Brown

    Unbeaten Big Brown won the 2008 Derby from post 20, then was eased in the Belmont and finished last with the Triple Crown on the line.
    555pts
12. 12
    Smarty Jones

    The unbeaten Pennsylvania-bred took the 2004 Derby and Preakness, but Birdstone caught him in the Belmont before a record crowd of 120,139.
    555pts
13. 13
    American Pharoah

    The first Triple Crown winner in 37 years, ending a drought in 2015 with an electrifying performance at the Belmont.
    555pts
14. 14
    Regret

    Regret became the first filly to win the Derby in 1915, leading from start to finish in her first race as a three-year-old.
    555pts
15. 15
    Old Rosebud

    Old Rosebud won the 1914 Derby by eight lengths in a record 2:03 2/5, a winning margin that has been equaled but never beaten.
    555pts
16. 16
    Seattle Slew

    The first horse to sweep the Triple Crown while still unbeaten, in 1977, a feat matched only by Justify in 2018.
    470pts
17. 17
    Rich Strike

    An extraordinary 80-to-1 long shot who delivered the second-biggest upset in Derby history in 2022.
    470pts
18. 18
    Twenty Grand

    Twenty Grand set a Derby record of 2:01 4/5 in 1931 and added the Belmont, Travers and Jockey Club Gold Cup that year.
    470pts
19. 19
    Funny Cide

    Bought for $75,000 by a group of high-school friends, the gelding won the 2003 Derby and Preakness as the first New York-bred Derby winner.
    470pts
20. 20
    I'll Have Another

    I'll Have Another came from post 19 to win the 2012 Derby and took the Preakness, but a tendon injury forced him out the day before the Belmont.
    470pts
21. 21
    Mine That Bird

    Mine That Bird came from last at 50-1 to win the 2009 Derby by six and three-quarter lengths, a run that inspired the film 50 to 1.
    470pts
22. 22
    Whirlaway

    A popular and flashy 1941 Triple Crown winner known for his free-running style and distinctive long flowing tail.
    470pts
23. 23
    Spectacular Bid

    One of the greatest horses to win the Derby and Preakness (1979), narrowly missing the Triple Crown in the Belmont.
    470pts
24. 24
    Genuine Risk

    One of only three fillies to ever win the Kentucky Derby (1980), becoming an enduring fan favorite.
    470pts
25. 25
    California Chrome

    Bred from an $8,000 mare by two first-time owners, the California-bred colt won the 2014 Derby and Preakness and was twice voted Horse of the Year.
    370pts
26. 26
    Sunday Silence

    Sunday Silence won the 1989 Derby and an epic Preakness duel with Easy Goer, then was Japan's leading sire for 13 years running.
    370pts
27. 27
    Barbaro

    Barbaro won the 2006 Derby by six and a half lengths unbeaten, then shattered a leg in the Preakness and fought for eight months before laminitis ended his life.
    370pts
28. 28
    Assault

    King Ranch's Assault, who had a misshapen right front hoof, won the 1946 Derby by eight lengths on the way to the Triple Crown.
    252pts
29. 29
    Justify

    The 2018 unbeaten Triple Crown champion who incredibly never raced as a two-year-old before sweeping the Crown.
    0pts
30. 30
    Affirmed

    Affirmed beat Alydar in all three 1978 Triple Crown races, the last by a head in the Belmont, with 18-year-old Steve Cauthen riding.
    0pts
31. 31
    Count Fleet

    The 1943 Triple Crown winner took the Belmont by 25 lengths, a record until Secretariat, and was never beaten as a three-year-old.
    0pts
32. 32
    Silver Charm

    The grey colt held off Captain Bodgit in the 1997 Derby and won the Preakness, but Touch Gold denied him the Triple Crown in the Belmont.
    0pts
33. 33
    Omaha

    The third Triple Crown winner, in 1935, Omaha later shipped to England and was beaten a short head in the Ascot Gold Cup; he is buried in Omaha, Nebraska.
34. 34
    Swaps

    The 'California Comet' beat Nashua in the 1955 Derby, lost their famous match race in Chicago that August and went on to set five world records.
35. 35
    Majestic Prince

    A record $250,000 yearling, he beat Arts and Letters by a neck in the 1969 Derby and a head in the Preakness, then lost the Belmont to him.
36. 36
    Riva Ridge

    Penny Chenery's colt won the 1972 Derby and Belmont, and his earnings helped save Meadow Stable a year before his stablemate Secretariat swept the Triple Crown.
37. 37
    Winning Colors

    Only the third filly ever to win the Derby, she went wire to wire in 1988 for trainer D. Wayne Lukas and jockey Gary Stevens, holding off the colts.

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