Top Kentucky Derby Upsets Of All Times – Longshots Make It To Winner’s Circle

By Author: Lee Lane-Edgar
Total Articles: 365
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Not that upsets are not welcome but what would you call unpredictable in horse racing if it wasn’t the shocking emergence of some ‘underdog’, some ‘out of the fame lights race horse’ charging from behind, probably even stuck in the traffic for a while or duelled with a potential lead for majority of the race until it finally makes the ultimate plunge into unfathomable burst of speed to, say the least, settle for the winner’s circle, and especially do it when the circle belongs to the Kentucky Derby!
Donerail (1913 Kentucky Derby, Odds at 91-1)
The bay colt by Hanover won no more than 10 races of his 62 starts. However, the Derby was meant to be. Despite competing with crucial fast pacers like Ten Point and Yankee Notions, Denerail is remembered to have been in safe striking distance and he remained there until the final turn. His upset is the greatest in the racing history and during the race; Donerail set a new track record, just a seconds more than the current record of approx. 2:00 minutes. He hit the wire half a length ahead of Ten Point and in 2:04 4/5. Bettors were paid as much as $184.90 for a ...
... $2 bet!
Mine That Bird (2009 Kentucky Derby, Odds at 51-1)
Calvin Borel, also famous for his Go-Rail riding techniques, had kept Mine That Bird neatly tucked along the rail for majority of the distance. The race had other stronger leads like Musket Man and Pioneerof the Nile, who looked as top prospects for the winning positions. However tables turned and the duo hanging around the rail burst into speed charging away from the field into a victory by six and three quarters incredible lengths. The longest shot after Donerail, Mine That Bird paid off $103!

Giacomo (2005 Kentucky Derby, Odds at 50-1)
This was sired by Holy Bull, who himself finished 12th in the Derby at 2-1 odds after having bumped when charging out of the starting gate. Giacomo rewrote history becoming one of the highest paid winners in the event’s history paying the winner a whopping $1,639,600. Ridden by award winning jockey, Mike Smith, Giacomo nailed the Derby in 2:02.75.

Gallahadion (1940 Kentucky Derby, Odds at 36-1)
He was foaled in 1937 and sired by the renowned Sir Gallahad III who was a champion sire of the 1930s. What brought Gallahadion to the fore was his Derby finish at Churchill Downs against timeless racehorse Bimelech. Having won only 6 out of the 36 starts, Gallahadion marked another memorable upset in the history of Derby after a decent longshot by Exterminator in 1918.

Charismatic (1999 Kentucky Derby, Odds at 31-1)
Kentucky Derby’s 125th run was dominated by a longshot upsetting the entire race at odds of 31-1. Not a track record establishing race but a decent pull across the 1 ¼ miles in 2:03.20 made Charismatic an instant winner. His pedigree boasted of racing legends like Secretariat and Northern Dancer but with only 5 wins out of 17 starts, including the Derby, Charismatic was close to his charisma in the Preakness and Belmont Stakes right after which, this Triple Crown probable ended up in stall following a close to fatal leg fracture.
There have been many other upsets in the sport’s history but to be one in Kentucky Derby makes race horse truly special as he competes against the choicest of top class racing prodigies who have proven themselves time and again to earn a spot there.
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