In 2008, Desormeaux won his third Kentucky Derby aboard Big Brown who won easily by just under five lengths. Two weeks later, Desormeaux rode Big Brown to victory in the Preakness Stakes at Pimlico Race Course, this time winning by just over five lengths while in hand. With a Triple Crown on the line, Big Brown was made the heavy 3-10 favorite in the Belmont Stakes. Unfortunately, Big Brown broke poorly and was rank for the first quarter mile. He finally settled, but had no response when Desormeaux asked him to run. Desormeaux eased Big Brown after the colt tired at the quarter pole. It was an inexplicably poor performance by a colt who went on to win the Haskell Invitational and Monmouth Park Stakes. Desormeaux received a good deal of criticism for his ride, though some praised him for protecting the colt from potential injury.