Hill Gail was a dark bay horse bred and raced by Calumet Farm of Lexington, Kentucky. He was sired by Champion sire Bull Lea out of Jane Gail, a successful but temperamental racemare described by her trainer Jimmy Jones as "a well-authenticated bitch".^[1] As a descendant of the broodmare St Angela, Jane Gail was distantly related to the British champion St. Simon and Orme.^[2]

Hill Gail was trained by Ben Jones for races in the East while his son Jimmy handled the colt's conditioning in California.

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.^[3] In October, Hill Gail recorded an upset victory over the year's leading colt Tom Fool in a sprint race at Belmont Park,^[4] 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.^[5] Hill Gail set a new Churchill Downs track record of 1:34.4 for eight furlongs when winning the Derby Trial by six lengths, and became only one of five horses to win both the Derby Trial and the Kentucky Derby.^[6] With Tom Fool ruled out by illness,^[7] Hill Gail became the popular choice for the Kentucky Derby.^[8]

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 and had the largest crowd to date at 110,000.^[9] When Hill Gail began to misbehave in the paddock before the race, Ben Jones reportedly calmed the horse by punching him on the nose.^[1] 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"^[10] 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 favorite 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.^[11] The winning time of 2:01 3/5 was the second fastest time to date.^[9] Hill Gail sustained a leg injury in the Derby which prevented him from running in the Preakness and Belmont Stakes.^[12]

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.

In 1954, Hill Gail was sold for $150,000^[13] and exported to be sent to Ireland where he stood as a stallion at the Brownstown Stud. The most successful of Hill Gail's offspring was Martial who won the Classic 2000 Guineas in 1960. However, Hill Gail's other offspring met with only limited success in racing on European grass surfaces. He died there in 1968. A plaque to his memory is in the Calumet Farm horse cemetery.^[14]