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Top 37 Most Famous Preakness Stakes Winners of All Time

By YPB Team

The Preakness Stakes has witnessed some of the greatest thoroughbreds in history thunder down the Pimlico stretch over 150 years. Who stands as the most legendary winner of the second jewel of the Triple Crown?

  1. Secretariat — ranked #11
    Secretariat
    The 1973 Triple Crown champion who holds the Preakness Stakes' fastest official time (1:53.00) and is widely regarded as the greatest racehorse in history.
    1000pts
  2. Real Quiet — ranked #22
    Real Quiet
    The 1998 Derby and Preakness winner who lost the Triple Crown by a nose to Victory Gallop in one of the Belmont's most painful photo finishes.
    653pts
  3. War Emblem — ranked #33
    War Emblem
    The 2002 Kentucky Derby and Preakness winner who led both races wire to wire before stumbling at the start of the Belmont.
    625pts
  4. Big Brown — ranked #44
    Big Brown
    The undefeated 2008 Kentucky Derby and Preakness winner whose Triple Crown bid ended when he was eased in the Belmont Stakes.
    625pts
  5. Nashua — ranked #55
    Nashua
    The 1955 Preakness winner who set a stakes record that year and later avenged his Derby loss by beating Swaps in a famous match race.
    625pts
  6. Sunday Silence — ranked #66
    Sunday Silence
    The 1989 Derby and Preakness winner whose nose victory over Easy Goer in the Preakness stretch duel is among the race's greatest finishes.
    574pts
  7. Afleet Alex — ranked #77
    Afleet Alex
    The 2005 winner who clipped heels with Scrappy T and nearly fell at the top of the stretch, then recovered to win by almost five lengths.
    574pts
  8. Funny Cide — ranked #88
    Funny Cide
    The 2003 Preakness winner who was the first New York-bred gelding to win the Kentucky Derby and Preakness, becoming a national sensation before falling just short of the Triple Crown.
    515pts
  9. Charismatic — ranked #99
    Charismatic
    The 31-1 Kentucky Derby longshot who won the 1999 Preakness and was named Horse of the Year after a career-ending injury in the Belmont.
    515pts
  10. Justify — ranked #1010
    Justify
    The 2018 Triple Crown winner who became only the second undefeated Triple Crown champion in history, accomplishing the feat without ever racing as a two-year-old.
    515pts
  11. Assault — ranked #1111
    Assault
    The 1946 Triple Crown winner from Texas' King Ranch, nicknamed the 'Club-Footed Comet' for overcoming a deformed hoof to sweep the series.
    515pts
  12. Canonero II — ranked #1212
    Canonero II
    The Venezuelan-trained $1,200 yearling who won the 1971 Kentucky Derby as a longshot and then the Preakness in record time.
    515pts
  13. Point Given — ranked #1313
    Point Given
    Bob Baffert's towering chestnut who won the 2001 Preakness and Belmont and was named Horse of the Year.
    446pts
  14. California Chrome — ranked #1414
    California Chrome
    The California-bred people's horse who won the 2014 Kentucky Derby and Preakness and later became a two-time Horse of the Year.
    446pts
  15. Damascus — ranked #1515
    Damascus
    The 1967 Preakness and Belmont winner and Horse of the Year, famous for crushing Buckpasser and Dr. Fager in the 'Race of the Century'.
    446pts
  16. War Admiral — ranked #1616
    War Admiral
    The 1937 Triple Crown champion, son of Man o' War, remembered not only for his Preakness win but for his legendary match race loss to the populist hero Seabiscuit the following year.
    446pts
  17. I'll Have Another — ranked #1717
    I'll Have Another
    The 2012 Kentucky Derby and Preakness winner who was scratched from the Belmont with a tendon injury the day before his Triple Crown attempt.
    446pts
  18. Whirlaway — ranked #1818
    Whirlaway
    The 1941 Triple Crown winner known as 'Mr. Longtail' for his distinctive long, flowing tail, famous for his dramatic come-from-behind racing style under trainer Ben Jones.
    446pts
  19. Silver Charm — ranked #1919
    Silver Charm
    The gray 1997 Kentucky Derby and Preakness winner who narrowly missed the Triple Crown and later won the 1998 Dubai World Cup.
    446pts
  20. Northern Dancer — ranked #2020
    Northern Dancer
    The small Canadian colt who won the 1964 Kentucky Derby and Preakness and became the most influential Thoroughbred sire of the 20th century.
    365pts
  21. American Pharoah — ranked #2121
    American Pharoah
    The 2015 Triple Crown winner who ended a 37-year drought without a champion, making him the first horse since Affirmed in 1978 to sweep the Kentucky Derby, Preakness, and Belmont.
    365pts
  22. Smarty Jones — ranked #2222
    Smarty Jones
    The feel-good 2004 Preakness winner who shattered the margin of victory record by 11.5 lengths, captured America's hearts, and came agonizingly close to the Triple Crown before finishing second at Belmont.
    365pts
  23. Rachel Alexandra — ranked #2323
    Rachel Alexandra
    The 2009 winner who became the first filly in 85 years to win the Preakness and was named Horse of the Year.
    365pts
  24. Affirmed — ranked #2424
    Affirmed
    The 1978 Triple Crown winner whose epic rivalry with Alydar — who finished second in all three races — produced one of the greatest sporting rivalries in history.
    365pts
  25. Omaha — ranked #2525
    Omaha
    The 1935 Triple Crown winner and son of Gallant Fox, still the only Triple Crown champion sired by another Triple Crown winner.
    365pts
  26. Citation — ranked #2626
    Citation
    Eddie Arcaro's 1948 Triple Crown winner, a powerhouse who won 16 straight races and became racing's first million-dollar earner.
    365pts
  27. Sir Barton — ranked #2727
    Sir Barton
    The first Triple Crown winner in 1919, who won the Preakness just four days after his Kentucky Derby victory and before the series even had its name.
    268pts
  28. Gallant Fox — ranked #2828
    Gallant Fox
    The 1930 Triple Crown winner ridden by Earl Sande, the horse whose sweep inspired the term 'Triple Crown' in American racing.
    268pts
  29. Seattle Slew — ranked #2929
    Seattle Slew
    The 1977 Triple Crown winner who became the first horse to sweep the series while still unbeaten.
    268pts
  30. Bold Ruler — ranked #3030
    Bold Ruler
    The 1957 Preakness winner and Horse of the Year who went on to become an eight-time leading sire, most famously of Secretariat.
    268pts
  31. Spectacular Bid — ranked #3131
    Spectacular Bid
    The brilliant gray who won the 1979 Kentucky Derby and Preakness, missed the Triple Crown at the Belmont, and finished with 26 wins in 30 starts.
    268pts
  32. Alysheba — ranked #3232
    Alysheba
    The 1987 Kentucky Derby and Preakness winner who later captured the 1988 Breeders' Cup Classic and Horse of the Year honors.
    268pts
  33. Count Fleet — ranked #3333
    Count Fleet
    The 1943 Triple Crown winner who took the Preakness by eight lengths and the Belmont by 25, never losing a race as a three-year-old.
    0pts
  34. Swiss Skydiver — ranked #3434
    Swiss Skydiver
    The 2020 Preakness Stakes winner and one of only six fillies to have ever won the race, defeating a field of colts in a dramatic victory that capped a remarkable season.
    0pts
  35. Native Dancer — ranked #3535
    Native Dancer
    The 'Gray Ghost', early television's first equine star, who won the 1953 Preakness and Belmont and lost only once in 22 career starts.
    0pts
  36. Curlin — ranked #3636
    Curlin
    The 2007 Preakness winner who beat Derby champion Street Sense by a head and went on to be a two-time Horse of the Year.
    0pts
  37. Man o' War — ranked #3737
    Man o' War
    The legendary chestnut who skipped the 1920 Kentucky Derby but won the Preakness on his way to 20 victories in 21 career starts.
    0pts

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