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Kentucky'd/pulling a Kentucky means when one is ever so close to achieving a milestone or a great deal of success, but fails disappointingly.
Derives from the 2015 NCAA March Madness Tournament (basketball) in which Kentucky almost had a perfect season but lost to Wisconsin in the semi-finals 71-64, forcing their record to be a 38-1.
Young Jack was expected to take honors classes, and so he did. The next year, he failed every single one of his classes. I guess you could say his teachers Kentucky'd him.
by Fruitsoftheworld April 07, 2015
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