Ranking the 10 Biggest Upsets in Preakness History

Jessica Paquette@jmpaquetteFeatured ColumnistMay 13, 2015

Ranking the 10 Biggest Upsets in Preakness History

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    Patrick Smith/Getty Images

    Though the Preakness Stakes is sometimes the forgotten middle child of the Triple Crown, the historic race has been the host of some of the biggest upsets and stunning defeats in horse racing history. Though favorites have reigned supreme for the most part, when they do falter, they fall hard.

    Fresh off a triumph in the Kentucky Derby, there have been favorites heading into the Preakness who looked like they simply could not lose. Further reiterating that there is no sure thing in horse racing, some of them did taste defeat. Some upset winners have come from nowhere, whereas others had been knocking on the door of a major win all year but were still overlooked.

    Here is a look at some of the biggest upsets in Preakness Stakes history, ranked by a combination of shock value, long odds and how much of a lock the favorite was. 

10. Charismatic, 1999

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    Doug Pensinger/Getty Images

    The Favorite: Menifee, the runner-up in the 1999 Kentucky Derby, looked poised to seek his revenge on Charismatic.

    The Spoiler: Charismatic, the upset winner of the Kentucky Derby at odds of 31-1, was out to prove his Derby triumph was not a fluke.

    How It Happened: Charismatic was given no respect at the windows and went off at odds of 8-1. While not an astronomical price, it was a shock for the Kentucky Derby winner to be the fourth choice on the betting odds. Charismatic proved that he was the real deal and soundly defeated Menifee for the second consecutive time. 

9. Red Bullet, 2000

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    The Favorite: Fusaichi Pegasus, the Kentucky Derby winner hailed as the next superhorse, was well-backed in the second jewel of the Triple Crown and went off as the overwhelming odds-on favorite. 

    The Spoiler: Red Bullet, a relative unknown, had skipped the Kentucky Derby after a runner-up effort in the Wood Memorial (G1).

    How It Happened: Fusaichi Pegasus could not lose...until he did. He was unable to recapture the glory he had in Kentucky and turned in a flat performance to finish second, 3 ¾ lengths behind Red Bullet, who drew away convincingly in the stretch. 

8. Hansel, 1990

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    The Favorite: Strike the Gold had defeated the favored Hansel just weeks before in the Kentucky Derby.

    The Spoiler: Hansel, despite his favoritism in the Kentucky Derby, was overlooked and went off at odds of 9-1 as he sought revenge for his Kentucky Derby defeat.

    How It Happened: Facing a field of only seven rivals, Hansel was able to get an ideal trip and rate off the front-runner Corporate Report. He drew off to win by seven lengths, denying Strike the Gold a chance at the Triple Crown and leaving folks to wonder what if the horse had had a better day at the Derby. 

7. Louis Quatorze, 1996

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    BILL SIKES/Associated Press

    The Favorite: Cavonnier, the runner-up in the 1996 Kentucky Derby, was fresh off his heart-breaking defeat by a nose in the Run for the Roses.

    The Spoiler: Louis Quatorze had never won a stakes race going into the Preakness Stakes, and it was not for lack of opportunity. He was also 16th in the Kentucky Derby with no apparent excuse.

    How It Happened: With a sharp break, Louis Quatorze was able to seize the lead, and that was all he needed to make every call a winning one and score at odds of 8.5-1. The horse that finished second, Skip Away, would go on to be one of the greatest stars of his generation.

6. Shackleford, 2011

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    Matt Slocum/Associated Press

    The Favorite: Though he was a long shot when he won the Kentucky Derby two weeks before, the public quickly came around on Animal Kingdom and made him the favorite for the second jewel of the Triple Crown.

    The Spoiler: Shackleford, despite a game fourth-place finish in the Kentucky Derby, had never won a stakes race and at that point looked like he was a cut below the top horses. His odds reflected that, and he was sent off at almost 13-1. 

    How It Happened: Shackleford brought his running shoes and, despite a bobble at the start, went to the front end to put pressure on the pace-setter. He seized command at the top of the stretch and had enough left to hold off Animal Kingdom and deny him his chance at the Triple Crown. 

5. Bernardini, 2006

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    JIM DIETZ/Associated Press

    The Favorite: Barbaro, the hero in the Kentucky Derby, looked nearly unbeatable as he approached the starting gate at odds of 1-2.

    The Spoiler: Bernardini, despite his royal pedigree and rising star, was unproven and untested and sent off at odds of nearly 13-1.

    How It Happened: Barbaro suffered a catastrophic injury after the beginning of the race, and Bernardini rolled to an effortless, though bittersweet, 5 ¼ length victory. No one will ever know if the outcome of the race would have been different had Barbaro not been injured. 

4. Master Derby, 1975

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    The Favorite: Foolish Pleasure was the winner of the Kentucky Derby and the reigning champion juvenile. 

    The Spoiler: Master Derby finished fourth in the Kentucky Derby. At odds of 23-1, his chances of turning the tables on Foolish Pleasure seemed unlikely.

    How It Happened: Master Derby got his Kentucky Derby redemption and defeated Foolish Pleasure by one length. In doing so, he became the biggest long shot in Preakness history to win. 

3. Deputed Testamony, 1983

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    The Favorite: Sunny's Halo, the winner of the 1983 Kentucky Derby, looked to take his sharp cruising speed to another forwardly placed victory. 

    The Spoiler: Deputed Testamony, a Maryland-bred horse, was making his fifth start in less than eight weeks and loomed as a big long shot at nearly 15-1.

    How It Happened: Deputed Testamony pulled off the shocker on the off track and ran the race of his career to win by two lengths. He is the last Maryland-bred colt to win the Preakness Stakes and at the time of his death in 2012 at the age of 32 was the oldest living winner of a Triple Crown race. 

2. Bee Bee Bee, 1972

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    Uncredited/Associated Press

    The Favorite: Riva Ridge looked like one of those horses that simply could not lose. After winning the Kentucky Derby, the colt seemed like the heir to the Triple Crown, and the Preakness would be just a formality.

    The Spoiler: Bee Bee Bee, winner of a minor stakes race at Pimlico the previous month, looked like he was in over his head at odds of almost 19-1.

    How It Happened: Riva Ridge showed an immediate dislike of the off track and wound up struggling and finished fourth. Bee Bee Bee, on the other hand, splashed home in the slop to win by 1 ½ lengths. Riva Ridge would go on to win the Belmont Stakes, making Bee Bee Bee not only just a Preakness spoiler but the one who denied him the Triple Crown. 

1. Oxbow, 2013

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    Matt Slocum/Associated Press

    The Favorite: Orb delivered as the favorite in the 2013 Kentucky Derby, and from the moment he crossed the finish line, he seemed like the most legitimate Triple Crown contender in years.

    The Spoiler: Oxbow had struggled through his sophomore season and was sent off at odds of 15-1 after finishing sixth in the Kentucky Derby.

    How It Happened: D. Wayne Lukas and Gary Stevens reunited for a magical upset victory. In a bold, confident ride by the legendary jockey, Stevens and Oxbow coasted through pedestrian fractions and had more than enough left to steal the race on the front end to win by 1 ¾ lengths. 


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