Bull Stakes but was never in contention and was eased down in the closing stages by his rider Javier Castellano to finish ninth of the eleven runners behind Cairo Prince. Jose Lezcano became the fourth jockey to ride the colt when he was dropped in class to contest an allowance race on February 22. He appeared outpaced in the early stages but passed tiring rivals in the straight and finished fourth of the ten runners behind Constitution. In April, Wicked Strong was moved north for the Grade I Wood Memorial Stakes at Aqueduct, a major trial race for the Kentucky Derby. The betting market was dominated by the unbeaten colts Social Inclusion and Samraat, and Wicked Strong, ridden by Maragh, started at 9.2/1. The colt settled on the inside before switching out and turning into the straight in fourth place. He overtook Social Inclusion inside the final furlong and drew away to win "readily" by three and a half lengths. In the 2014 Kentucky Derby, Wicked Strong, the 6.5/1 second favorite, drew number 20 post position, on the far outside of the field. Jerkens admitted that the draw was disadvantageous and commented that "my dad was bummed about it" but also said that "at least he won't have anybody from the outside banging him in there". After stumbling on leaving the gate Wicked Strong was forced five wide on the first turn and was towards the back of the field for most of the way. He was in tenth place with a quarter mile left to run but made steady progress to finish fourth behind California Chrome, Commanding Curve and Danza. Wicked Strong's connections opted to bypass the Preakness Stakes and reappeared in the Belmont Stakes on June 7 when he was one of ten colts attempting to prevent California Chrome from winning the Triple Crown. Starting the 5.3/1 second favorite he raced in mid-division before turning into the straight in sixth. He made steady progress on the wide outside in the closing stages but never looked likely to win, eventually dead-heating with California Chrome for fourth, two lengths behind the winner Tonalist. On July 26, Wicked Strong started second favorite behind Tonalist in the Jim Dandy Stakes over nine furlongs at Saratoga Race Course. Equipped with blinkers for the first time he raced much closer to the lead than usual, went to the front approaching the final turn and