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1. Dark Star ($51.80) in 1953. It was the only loss in 22 starts for Native Dancer, who went off as the 7-10 favorite.
2. Donerail ($184.90) in 1913. By beating Ten Point, the 6-5 favorite, Donerail rewarded his backers with what is still the largest Derby payoff.
3. Zev ($40.40) in 1923. Only five horses in the 21-horse field went off at higher odds. That's because Zev had finished next to last in the Preakness, then run a week before the Derby.
4. Canonero II ($19.40) in 1971. Shipped from Venezuela on a plane carrying farm animals, he paid so little because he had been placed in the pari-mutuel "field."
5. Bold Venture ($43) in 1936. Brevity, the 4-5 favorite, was knocked down, and Granville, who may have been the best horse in the race, unseated his rider at the start.
6. Proud Clarion ($62.20) in 1967. The best horse was Damascus, who finished an inexplicable third. Proud Clarion won only six of 25 career starts.
7. Gallahadion ($72.40) in 1940. Bimelech, the runner-up and 2-5 favorite, was running in his third race in nine days.
8. Chateaugay ($20.80) in 1963. How do you figure him beating two unbeaten horses, Candy Spots and No Robbery?