Ranking the Biggest Upsets in Kentucky Derby History

Jessica Paquette@jmpaquetteFeatured ColumnistApril 28, 2015

Ranking the Biggest Upsets in Kentucky Derby History

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    Matt Slocum/Associated Press

    In horse racing, the only thing that is certain is that absolutely nothing is certain. At the Kentucky Derby, anything can happen. With a field of 20 three-year-olds all vying for a spot in the history books, the race is always primed for a major upset.

    The winning horse is not always the best horse. The Kentucky Derby is the race that can define a horse’s career, and sometimes, all it takes is a little bit of luck and the race of his or her life for a horse to rise from the unknown to the winner’s circle.

    Here is a look at some of the biggest upsets in the history of the Kentucky Derby!

8. Donerail, 1913

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    David J. Phillip/Associated Press

    How It Happened: Though the records from the early days of the Kentucky Derby are at times obscure, there is no question that Donerail shocked the nation with a stunning upset at odds of 91-1 in the 1913 running. He rallied from off the pace to win by half a length.

    Why It Was Shocking: His upset victory returned $184.90 on a $2 win wager. To this date, that remains the biggest $2 win payout in Kentucky Derby history, and his winning odds are shocking even by modern-day standards.

    Why It's Here: At astronomical odds, he holds the title as the longest shot to ever win the Run for the Roses, which has cemented him a permanent place in the history books. 

7. Animal Kingdom, 2011

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    David J. Phillip/Associated Press

    How It Happened: The day before the 2011 Kentucky Derby, the horse that was likely to be the overwhelming favorite, Uncle Mo, scratched out of the race, sending even the sharpest handicapper back to the drawing board. With Uncle Mo out of the picture, the tote board became wide open, and Dialed In went off as the favorite at a lukewarm 5-1.

    Why It Was Shocking: Animal Kingdom was overlooked at 21-1 and was the 11th choice in the field. He was a long shot for a reason—until that point, he was unproven on conventional dirt and had only run on turf and synthetics. As he began his rally from off the pace, there was no question that he was taking to the new surface. 

    Why It's Here: While the payoff was large at double-digit odds, the real shock came because of Uncle Mo's defection, which left the door open for a new champion to take center stage. Animal Kingdom was not a one-hit wonder, though. He went on to have a successful career and won the Dubai World Cup at four years old. 

6. Go for Gin, 1994

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    How It Happened: Torrential rain hit Louisville before the Kentucky Derby in 1994 and rendered the track a sloppy mess. Holy Bull had at that point won eight of his nine starts, and the blanket of roses seemed all but a given as the horses loaded into the starting gate. 

    Why It Was Shocking: Holy Bull wound up turning in one of the rare poor performances of his career and finished 12th at odds of 2-1. Go For Gin relished the off-track and stole the race on the front end, splashing home to win by two lengths at odds of 9-1. 

    Why It's Here: In the case of the 1994 Kentucky Derby, it was not so much that Go For Gin was a huge long shot; it was simply that Holy Bull looked too good to lose. His dismal performance left many people scratching their head. 

5. Charismatic, 1999

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    AL BEHRMAN/Associated Press

    How It Happened: Sent off at odds of 31-1 and hopelessly overlooked, Charismatic gave the racing world another reminder to never count out trainer D. Wayne Lukas. Under a textbook perfect ride from jockey Chris Antley, the chestnut colt rated off the pace and prevailed to win by a neck. The favorites, General Challenge and the filly Excellent Meeting—both from Golden Eagle Farmfinished fifth and 11th, respectively. 

    Why It Was Shocking: Charismatic barely earned his way into the Kentucky Derby starting gate. It was a victory in the Coolmore Lexington Stakes just 13 days that secured his spot in the race. Prior to that, both of his career victories had come against claiming competition.

    Why It's Here: Going from claiming races to the Kentucky Derby is the ultimate rags-to-riches story. With Charismatic, Lukas and Antley, the stars aligned for something magical to happen, and they cemented their spot in the history books. 

4. Gato Del Sol, 1982

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    How It Happened: The third-longest shot on the board, Gato Del Sol flew under everyone's radar and pulled a massive upset to win the 1982 Kentucky Derby at odds of 21-1. Though the field that assembled was arguably one of the weakest in recent years, he rallied from last to first to win by 2 ½ lengths.

    Why It Was Shocking: Though he had won the prestigious Del Mar Futurity as a juvenile, his three-year-old season had been less inspiring. From four races as a sophomore, he had failed to win and was fourth in the Santa Anita Derby in his final prep, leaving questions as to whether or not he had peaked as a two-year-old. 

    Why It's Here: He pulled off the victory at generous odds and justified his trainer Eddie Gregson's faith in the colt. As Gregson told Steven Crist of The New York Times in 1982, "I never stopped believing in this horse. Sometimes I doubted myself and the jockey, but never the horse.''

3. Lil E Tee, 1992

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    How It Happened: Jockey Pat Day was always known for his patience in the saddle, and the 1992 Kentucky Derby was no exception. Overlooked at odds of 17-1, Lil E Tee launched a bold bid from off the pace and won by a length. Behind him through eighth place, the other horses all finished with double-digit odds as well. 

    Why It Was Shocking: Arazi, who wound up finishing eighth, was heralded as a super-horse in the making, and the betting public viewed him as nearly unbeatable as the odds-on favorite. The horse that seemingly had the potential to be his biggest challenger, A.P. Indy, had to defect from the race earlier in the week. Without that competition, Arazi seemed like a lock.

    Why It's Here: Lil E Tee's victory stunned the racing world as it watched the international chestnut hero, Arazi, finish eighth. In the history of Kentucky Derby favorites, Arazi was one of the biggest. 

2. Giacomo, 2005

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    How It Happened: Giacomo was able to succeed in the 2005 Kentucky Derby where his sire, Holy Bull, had failed in 1994. In one of the most thrilling finishes in Kentucky Derby history, the gray colt rallied desperately at odds of 50-1 to hold off fellow long shot Closing Argument and etch his spot in the history books. He prevailed by half a length. 

    Why It Was Shocking: With the much-hyped Bellamy Road sent off as the favorite and finishing a non-threatening seventh, the finish was a spectacular free-for-all with the two massive long shots beating Afleet Alex, who would go on to triumph in both the Preakness and the Belmont Stakes.

    Why It's Here: Giacomo left a lot of bettors and racing fans trying to figure out how he slipped off their radar. With only a maiden win to his credit prior to the Derby and a fourth-place finish in his most recent prep race, his stunning form reversal was a true shock. 

1. Mine That Bird, 2009

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    Jae C. Hong/Associated Press

    How It Happened: With the benefit of an off track and a textbook Calvin Borel rail-skimming ride, Mine That Bird was the horse that no one, not even announcer Tom Durkin, saw coming. The modestly bred gelding rolled to a 6 ½ length shocker at odds of 50-1.

    Why It Was Shocking: Though there was no major standout in the race and Friesan Fire was sent off as the favorite at 4-1 odds, Mine That Bird appeared to be one of the contenders least likely to pull off an upset. He exploded onto the scene in a last-to-first run from off the pace and became a household name.

    Why It's Here: Mine That Bird, with his cowboy-hat wearing trainer Ben Wooley Jr. a complete unknown as well, was a captivating long shot. The upset victory was so visually stunning that he left both his competitors and the audience asking themselves, "Who was that horse?" He would never win again. 

    All odds via Equibase.com.