 In 1986, he got his big break when Ogden Phipps hired him to train his stable of horses.In 1988, McGaughey won the Eclipse Award for Outstanding Trainer in the United States.Among his many wins, he has captured the Jockey Club Gold Cup three times, the Travers Stakes four times, and won the 1989 Belmont Stakes with Hall of Fame Champion Easy Goer as well as the 2013 Kentucky Derby with Orb.