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10 Biggest Kentucky Derby Long Shots

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2012 will mark the 138th running of the Kentucky Derby at Churchill Downs, the most important race in North America for 3-year-old thoroughbreds. Here is a list of the 10 biggest paying long shots to ever win the "Run for the Roses."

1. Donerail 1913

Donerail's sign on the grandstand at Churchill Downs
© Cindy Pierson Dulay
Sent off at odds of 91.45-1, Donerail paid $184.90 to win in 1913 which is still the highest paying winner ever in the Kentucky Derby.

Each Kentucky Derby winner has their name on a sign on the back of the grandstand at Churchill Downs. To the left is Donerail's sign.

2. Mine That Bird 2009

Mine That Bird
© Cindy Pierson Dulay
Mine That Bird trailed most of the race before rallying down the inside in the stretch to win by 6 3/4 lengths at odds of 50.60-1, paying $103.20 to win in 2009. He went on to finish second in the Preakness to Rachel Alexandra and third in the Belmont behind Summer Bird and Dunkirk. He was a gelding and continued racing until November 2010 but never recaptured his Kentucky Derby glory, going winless in the nine times he races afterwards before he retired.

3. Giacomo 2005

Giacomo wins the 2005 Kentucky Derby
© Cindy Pierson Dulay
In 2005, Giacomo closed late on the far outside to in at odds of 50.30-1 and paid $102.60 to win, second highest in Kentucky Derby history.

4. Gallahadion 1940

Gallahadion
Churchill Downs Inc.
In 1940, Gallahadion won at odds of 35.20-1 and paid $72.40 to win, the third highest in Kentucky Derby history.

5. Charismatic 1999

Charismatic at the 1999 Kentucky Derby
© Cindy Pierson Dulay
Charismatic went off at odds of 31.30-1 and just got up to win by a neck, paying $64.60 to win. He went on to win the Preakness and was 3rd in the Belmont where he broke his leg after the finish. Jockey Chris Antley pulled him up and kept his leg off the ground until the vet arrived. He had surgery the next day and is currently standing at stud in Japan at Iburi Stallion Station.

6. Proud Clarion 1967

Proud Clarion won in 1967 at odds of 30.10-1 and paid $62.20 to win, the 5th highest in Kentucky Derby history. He also had the 6th fastest Derby win ever with a final time of 2:00.60 for the mile and a quarter.

7. Exterminator 1918

In 1918, Exterminator may have been a surprise when he won the Kentucky Derby at odds of 29.60-1, paying $61.20 to win, but he went on to have a stellar career. Racing until age 9, the gelding won 50 of he 100 lifetime starts including many stakes races and was very popular with fans.

8. Dark Star 1953

Dark Star won in 1953 at odds of 24.90-1 and paid $51.80 to win, the 7th highest ever in the Kentucky Derby. Also the winner of the Derby Trial, he was unplaced in Preakness and retired after that.

9. Thunder Gulch 1995

Thunder Gulch at Ashford Stud in 2007
© Terence Dulay
Sent off at odds of 24.50-1, the longest of the three horses entered by trainer D. Wayne Lukas in 1995, Thunder Gulch drew off to win by 2 1/4 lengths and paid $51.00 to win. He went on to be 3rd in the Preakness and won the Travers Stakes and the Kentucky Cup, retiring to stud at the end of his 3-year-old season.

10. Stone Street 1908

Stone Street went off at odds of 23.72-1 in the 1908 Kentucky Derby and paid $123.60 to win for a $5 bet which would be $49.40 for the modern $2 win bet. This was the only stakes win of his career.
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