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Eddie Arcaro [February 19, 1916 - November 4, 1997] is considered the best rider to have ever played at the Kentucky Derby. Specifically, Arcaro is a five-time Kentucky Derby winner. He in fact is considered the greatest jockey in American horse racing history. That honor comes from the fact of his being one of only two jockeys to win the Derby five times. But he also is the only jockey to have won the U.S. Triple Crown twice: in 1941 on Whirlaway, and in 1948 on Citation.

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Q: Who is the best rider who ever played at the Kentucky Derby?
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