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Come Fan with UsSunday, June 21, 2026

Preakness Winner Shackleford, Jockey Jesus Castanon Stage Triple Crown Upset

Preakness winner Shackleford was the horse that looked least likely to do anything at the gate. As the 2011 Preakness field was being fed into the chutes at Pimlico, Shackleford balked repeatedly, looking unfocused and gleaming with sweat.

It turned out not to matter: Shackleford broke cleanly and swiftly, and burned a blazing first furlong in second place alongside fellow fast starter Flashpoint. But both horses slowed their pace slightly, giving Shackleford a chance to conserve a bit of energy while remaining out in front. That proved to be valuable when Kentucky Derby winner Animal Kingdom made his way through a massive pack in the middle of the track for a stretch run.

Animal Kingdom made a superb charge, especially in the final 300 yards, but Shackleford’s large lead helped him hold off Animal Kingdom’s challenge on the outside, and he won by three-quarters of a length.

Jockey Jesus Castanon gave an emotional interview from on top of Shackleford after winning his first Triple Crown race. “I know my dad is watching over me,” Castanon said, both in Spanish and in English. Castanon’s father died in November 2010.

Need more 2011 Preakness Stakes coverage? Check our Preakness StoryStream for odds, contender profiles, post positions and more. To look back at the Derby, check out SB Nation’s 2011 Kentucky Derby StoryStream. Also, our horse racing blog And Down The Stretch They Come has two must-read resources for Derby and Preakness fans: A Beginner’s Guide To Following Horse Racing and a glossary of horse racing terms.

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