5: Smarty Jones
Talk about an impressive family tree! Not only is Smarty Jones a third-generation descendant of the legendary Mr. Propsector, but also related to numerous recent Triple Crown hopefuls such as Funny Cide, Afleet Alex, and Fusaichi Peagasus.
Born in 2001, his roots also traces back to such greats as Secretariat and even the mighty Man O' War, and this pedigree likely had something to do with Smarty Jones taking top honors at both the Kentucky Derby and Preakness Stakes in 2004. Both wins along with his Sport Illustrated cover set off a national frenzy for the champion, who was thought to be a shoo-in for the Triple Crown. Surprisingly, he came in second after a stunning upset by 36-1 long shot Birdstone.