Many Kentucky Derby winners have gone into the Preakness as the heavy favorite, and though some of them came away with a victory, there are others that failed to capture the Woodlawn vase, ending their shot at a Triple Crown. Below are some of the notable Derby winners that did not repeat at Pimlico. Rank them in order of the most surprising upset, with #1 being the biggest shocker. To help with your rankings, there is a brief description of each upset listed below the ranking poll.
'34 Cavalcade - After a pretty handy Derby win, couldn't catch his stablemate High Quest, who had the the lead the entire race
'39 Johnstown - his speed carried at Churchill Downs, but he faded in the stretch at Pimlico, winding up a tiring fifth at 2-5 odds
'45 Hoop Jr. - was 6-5 in the Preakness, but Polynesian, who had skipped the Derby, won wire-to-wire
'56 Needles - only a second place finish, at 3-5 odds, in the Preakness denied this colt the Triple Crown
'72 Riva Ridge - a true disappointment after going off at 3-10, he would rebound to take the Belmont
'74 Cannonade - after beating 22 horses in the Derby, Cannonade was upset by a couple of double digit longshots in Little Current and Neapolitan Way
'75 Foolish Pleasure - Master Derby, at 23-1, shocked the 6-5 favorite.
'76 Bold Forbes - in just a six horse field, Bold Forbes checked in third behind the two of the longest priced horses in the field; Elocutionist and Play the Red
'83 Sunny's Halo - had no punch in the stretch run, finishing sixth at even money
'84 Swale - popular Derby winner was 4-5 at Pimlico, but ran uncharacteristically poor to wind up seventh
'90 Unbridled - fairytale Derby story came to an end when second to Summer Squall in Baltimore
'00 Fusaichi Pegasus - Failed to duplicate his Churchill effort when Red Bullet, who skipped the Derby, beat him by 3 3/4 lengths
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first place ranking will earn 11 points, second place receives 10 points, and so on.