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John Longden won on Count Fleet in 1943 as the jockey and trained 1969 winner Majestic Prince.

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15y ago

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That would be Calvin Borel on Rachel Alexandra for the Oaks and Mine that Bird for the Derby in 2009. Not sure who else has done it in the past, but that's the most recent.

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15y ago
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The 2009 winner was ridden by Calvin Borel.

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15y ago
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Ferdinand ridden by Bill (Willie) Shoemaker.

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15y ago
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Q: Jockey who won Kentucky Derby and also trained a Kentucky Derby winner?
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