From the start of the 1950 season, Hill Prince was regarded as one of the main contenders for the Triple Crown races, along with Oil Capitol, Middleground, and the Californian colt Your Host. On his seasonal debut he won the Experimental Handicap No. 1 at Jamaica, leading to him being promoted to challenge Oil Capitol as Derby favorite.
From the beginning of the 1950 racing season, Hill Prince was considered a strong contender for the Triple Crown races, along with Oil Capitol, Middleground, and Your Host. After winning his first race at Jamaica, he became the favorite to face off against Oil Capitol in the Derby.