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Giacomo, above, pulled off a shocker in the 2005 Kentucky Derby, but he wasn't the biggest longshot in the race's storied history. (Photo by

Mine That Bird’s amazing longshot victory in the 2009 Kentucky Derby still fascinates fans to this day. It’s now the subject of a film “50 to 1,” and has been on everyone’s lips as we get ready for this weekend’s 140th running of the Kentucky Derby.

Here is a look at some other notable upsets from years past: 

1. Donerail - 1913 – 91.45-to-1

Not much has been written about the longest shot to ever win the Kentucky Derby, but here’s what we can piece together. The 6-to-5 favorite in the 8-horse field that day was a horse named Ten Point, who had never raced farther than a mile. The overlooked Donerail had placed second in the Blue Grass Stakes under jockey Roscoe Goose, but then ran a disappointing fifth a few days later in the Camden Handicap in Lexington. For the Derby, Donerail was back under Roscoe Goose, a jockey who loved to ride longshots and knew the Churchill Downs track very well. He and Donerail made a good team. The horse paid $184.90 to win. 

2. Charismatic - 1999 – 31.30-to-1

There is no greater underdog story than that of Charismatic, Chris Antley and D. Wayne Lukas in the 1999 Kentucky Derby. Charismatic had competed in a claiming race earlier in the year and was available to anyone for $62,500. When the jockey who guided him to victory in the Coolmore Lexington Stakes opted for another contender in the race, Lukas went to Chris Antley, who less than a year earlier was overweight and considering retiring from the sport after battling substance abuse problems. Charismatic continued to shock the world when he won the Preakness (again, not the favorite) and came within an eighth of a mile of winning the Triple Crown in a dramatic finish that will never be forgotten. Chris Antley, having sensed that Charismatic was injured, lept from the horse on the track and cradled his leg in his arms to keep him from bearing down weight on it - probably saving the horse’s life.

3. Funny Cide - 2003 – 12.80-to-1

Funny Cide deserves a place on this list because he was one of the biggest longshots to win the Kentucky Derby when you consider everything that went right to get him to that point, even though 12-to-1 isn’t really a huge longshot on the tote board. A $22,000 yearling bought by a pinhooker and then sold to Sackatoga Stables, a partnership in upstate New York that included a teacher, a construction worker and a caterer, Funny Cide was not racing royalty. He had finished a respectable second in the Wood Memorial Stakes to the 5-to-2 Kentucky Derby favorite Empire Maker, and his morning line odds on Derby day were 15-to-1. He went on to win the Preakness and then miss the Triple Crown when third to his rival Empire Maker.

4. Giacomo - 2005 – 50.30-to-1

Everyone knows about the horse ranks just behind Mine That Bird with the third-highest payout in Kentucky Derby history. What often is forgotten about the 2005 Kentucky Derby is that Giacomo wasn’t the longest shot in the race. That honor belonged to Closing Argument who was 71.60-to-1, and Closing Argument ran second!! Closing Argument is actually the longest shot to ever finish second in a Kentucky Derby, paying $70 to place. The Giacomo-Closing Argument exacta paid $9,814.80! That payout set a Derby record, besting the old record of $1,300 by $8,500! While another 50-to-1 shot could win again (and did in 2009), it is unlikely we will ever see another 1-2 finish as big as we did in 2005. 

5. Gato Del Sol - 1982 – 21.20-to-1

Looking back, 1982 was a weird year for horse racing, mostly because of Gato Del Sol. He wasn’t one of the biggest prices to win the Kentucky Derby, but he’s notable for this list because he was so unlikely a winner that his own connections still considered it a fluke after the race. They opted out of racing him in the Preakness, the first time anyone had elected not to try for the Triple Crown in the prior 23 years. Coming back for the Belmont, Gato Del Sol lost by 14 lengths to Conquistador Cielo, the largest winning margin since Secretariat. Neither of the horses had run in the Preakness, which was won by third-choice Aloma’s Ruler. Conquistador Cielo had just won the Met Mile six days prior to the race and set a track record. If not for an injury, perhaps Conquistador Cielo could have won a Triple Crown!

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David Hill

David Hill is a writer and gambler who grew up in the shadow of the Oaklawn Park in Hot Springs, Ark. He has written for a number of publications and is currently writing his first book. You can read more at

Image Description

David Hill

David Hill is a writer and gambler who grew up in the shadow of the Oaklawn Park in Hot Springs, Ark. He has written for a number of publications and is currently writing his first book. You can read more at

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