Racing Career
At age two, Hill Gail set a new Arlington Park track record for six furlongs when winning the 1951 Arlington Futurity, the most valuable two-year-old race of the season. In October, Hill Gail recorded an upset victory over the year's leading colt Tom Fool in a sprint race at Belmont Park, but was beaten by the same colt in the Belmont Futurity five days later.
In early 1952, Hill Gail equaled the Keeneland Race Course record for six furlongs in winning the 1952 Phoenix Handicap but was twice defeated by the Irish colt Windy City. In the Santa Anita Derby however, he reversed the form to beat Windy City by four lengths. On the eve of the Kentucky Derby Hill Gail set a new Churchill Downs track record of 1:34.4 for eight furlongs when winning the Derby Trial by six lengths. With Tom Fool ruled out by illness, Hill Gail became the popular choice for the Kentucky Derby.
Hill Gail, ridden by the veteran jockey Eddie Arcaro, started betting favorite for the Kentucky Derby, which was broadcast across America on live television for the first time. When Hill Gail began to misbehave in the paddock before the race, Ben Jones reportedly calmed the horse by punching him on the nose. Eddie Arcaro sent the colt to the front after half a mile and Hill Gail produced what was described as a "stupendous burst of speed" to open up a six length advantage by the time the runners rounded the final turn. The outsider Sub Fleet emerged as a challenger in the stretch and Arcaro had to resort to his whip to ensure that Hill Gail reached the wire two lengths in front of Sub Fleet, with the second favourite Blue Man in third. The win gave Arcaro a record fifth Kentucky Derby, whilst trainer Ben Jones was winning the race for a sixth time, also a record. Hill Gail did not disappoint and won the first leg of the U.S. Triple Crown series by two lengths. Hill Gail sustained a leg injury in the Derby which prevented him from running in the Preakness and Belmont Stakes.
Racing at age four and again at age five, Hill Gail met with modest success, but did not win a significant Graded stakes race. At the end of the 1954 racing season, he was retired from racing.
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