TJ is right that Eddie Arcaro and Bill Hartack both rode in two attempts at the Triple Crown. Arcaro won both of his, finishing first aboard Whirlaway and Citation in 1941 and 1948, respectively. Hartack lost both of his, finishing third with Northern Dancer in 1964 and second with Majestic Prince in 1969. These are the two men I was thinking of.
If anyone alert has said to himself (or herself), "Wait, wasn't there someone else?", you're right. Kent Desormeaux rode two Derby/Preakness winners in the Belmont. The first time, he was second aboard Real Quiet in 1998. Then after Victor Espinoza made his first attempt at the Triple Crown with War Emblem in 2002, Desormeaux rode Big Brown, who officially failed to finish the 2008 Belmont. So there are three jockeys other than Espinoza, not two, who rode at least two Derby/Preakness winners in the Belmont. Mea culpa!
If anyone alert has said to himself (or herself), "Wait, wasn't there someone else?", you're right. Kent Desormeaux rode two Derby/Preakness winners in the Belmont. The first time, he was second aboard Real Quiet in 1998. Then after Victor Espinoza made his first attempt at the Triple Crown with War Emblem in 2002, Desormeaux rode Big Brown, who officially failed to finish the 2008 Belmont. So there are three jockeys other than Espinoza, not two, who rode at least two Derby/Preakness winners in the Belmont. Mea culpa!
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