For Hildreth, he was ridden by jockey Cal Shilling, Fitz Herbert earned back-to-back United States Horse of the Year awards. His major victories came in long races, something his trainer specialized in. In the 1909 Lawrence Realization Handicap, the horse set a world record for a 1-5/8 mile race.
In a deal described by the New York Times as the "biggest sale in years," in February of 1910 Hildreth sold Fitz Herbert for $40,000 to Charles Kohler, owner of Ramapo Stock Farm in Ho-Ho-Kus, New Jersey. Due to the legislated ban on parimutuel betting by the state of New York, a few weeks later Fitz Herbert and other horses owned by Kohler were shipped to stables at Maisons-Laffitte Racecourse in France where he was conditioned to compete in steeplechase racing.