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.
There have been many other upsets in the sport's history but to be one in Kentucky Derby betting 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. And speaking of upsets, I will share to you (for humor and laughs) the horse names that upsets me in the history of Kentucky Derby. Enjoy this too.
Gold Shower – 1943 Sure, you can say this horse’s name didn’t have the same meaning in the ’40s because back then there was nothing called a “golden shower.” But then what would you call what we did to the Axis powers? Woooooo! U-S-A! U-S-A!
Black Servant – 1921 Oh, olden days. Such a simpler time. And an incredibly more racist time. Black Servant was foaled at Idle Hour Stock Farm in Kentucky. Weird. I assumed 1920s Kentucky was far more progressive.
The Cock – 1916 The Cock only managed to place sixth at the 1916 Kentucky Derby. Probably because he had to lug around all that extra weight.
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