In 1946 a mare could have been bred to Princequillo, winner of the Jockey Club Gold Cup and conqueror of Bolingbroke and Shut Out in the Saratoga Handicap, for a mere $250. Recently purchased by Arthur Hancock, Sr., the bay son of Prince Rose was standing his first season at Ellerslie Stud in Charlottesville, Virginia. One of the breeders who sent a mare to Princequillo that year was rewarded with second place finishes in both the Epsom Derby and the Two Thousand Guineas four years later, when Princequillo's son Prince Simon earned championship honors in England. Christopher Chenery also bred to Princequillo in his first season, shipping his Bubbling Over mare Hildene to Ellerslie Stud that spring, and on February 20 of the following year she gave birth to her fourth foal at Chenery's Meadow Stud.

The bay son of Hildene and Princequillo, named Hill Prince, went into training with Casey Hayes in 1949. Hill Prince showed his talent immediately, when on July 2, 1949 he carried Eddie Arcaro to a seven length victory in a maiden special weight at Aqueduct.

A week later he won an allowance race by two lengths, this time with Doug Dodson in the irons. Casey Hayes didn't wait any longer before sending Hill Prince after added money. Unfortunately, the six furlong Sapling Stakes didn't give the colt enough ground to recover from a poor start, and he ran a fast closing second to Casemate.

After an easy win in allowance company, Hill Prince galloped to a five length win in the World's Playground Stakes. Ten days later he won the Babylon Handicap as the highweight, giving twenty pounds to runner up Miss Degree.

In the final start of his freshman campaign, Hill Prince scored an impressive two and a half length victory in the Cowdin Stakes, despite a sloppy track.

Wins in six of seven starts earned divisional honors for the Chenery colt, who shared the title of Champion Two Year Old Colt with Tom Gray's Oil Capital. It was Hopeful Stakes winner Middleground, however, who made top weight on the Experimental Free Handicap.

Middleground was a chestnut colt by 1936 Kentucky Derby and Preakness Stakes winner Bold Venture. Bred and raced by the King Ranch, Middleground had won four of his five starts at two, but his only stakes victory had been in the Hopeful, which kept him from championship honors. Hill Prince and Middleground were to meet on six occassions at three.

Hill Prince began his sophomore campaign in the Experimental Free Handicap. At the time, it was a real event, run at Jamaica in April. The first race was a six furlong sprint, and the second was held at a mile and a sixteenth. Hill Prince scored by a length and a quarter in the first event, but was the victim of racing luck in the second. He stumbled out of the gate, then spent the rest of the race battling traffic problems, finishing out of the money.

A week later he met Middleground for the first time, beating him by two lengths in the Wood Memorial. Then it was on to Churchill Downs. Fourteen colts went to post for the 1950 Kentucky Derby, including Experimental Free Handicap winner Lotowhite; C.V. Whitney's Mr. Trouble, winner of the Blue Grass Stakes; previous juvenile star and Flamingo Stakes winner Oil Capital; Santa Anita Derby winner Your Host, the future sire of Kelso; Brookmeade Stable's Sunglow, the future sire of Sword Dancer; Experimental Free Handicap highweight Middleground, who had run second in every one of his races at three, including the Derby Trial; Black George, the winner of the Derby Trial, and Hill Prince. Your Host was the post time favorite, with Hill Prince the second choice in the betting, despite having suffered a fever earlier in the week.

Oil Capital broke on top, then was taken back. Your Host and Mr. Trouble set the early pace, then were overtaken by Middleground as the field approached the head of the stretch. Hill Prince overcame traffic problems to make a move in the stretch, and despite being bumped by Your Host made a strong closing drive. Middleground held on to win, with Hill Prince second. Mr. Trouble was third after pushing the early pace.

Having each scored once against the other, Middleground and Hill Prince met again a week later in the Withers Stakes, and this time Hill Prince was the winner, leading into the stretch and drawing off to win by a length and a half. Both colts headed for Pimlico, as did Mr. Trouble.

Grantland Rice, who had seen many runnings of the Maryland Classic, wrote:

"They have more closely matched and better watched horses for 1950 -in a group- than I've ever seen in a Preakness, although I wasn't around when Survivor and Culpepper ran in 1873 and 1874. I doubt either could run with Hill Prince on even terms. Or with Middleground or Mr. Trouble."

Preakness Day was cold and gray, with a strong wind and a wet, sloppy track. Hill Prince met only five challengers, including his archrival Middleground, the C.V. Whitney entry of Mr. Trouble and the talented mudder Dooly, and two horses who had never even won a stakes race. They were Kinsman, a stakes placed son of Whirlaway, and Balkan, who at more than seventeen hands towered over the rest of the field.

Balkan beat out Mr. Trouble for the early lead, then faded as Hill Prince made his move, taking the lead after three-quarters of a mile. Middleground made a bold challenge, but Hill Prince just kept pulling away, winning by five lengths. Bill Boland, who rode Middleground to a second place finish, said:

"I was on a good, game colt, but we couldn't have beaten Hill Prince today had we gone on for five more miles."

Now the reigning star of his division, Hill Prince met older horses for the first time in the Suburban Handicap, but ran a disappointing third behind the good handicappers Loser Weeper and My Request. The cause was quickly evident; he had bled in the race.

Ten days later Hill Prince ran in the Belmont. He grabbed the early lead, then tired, finishing seventh behind Middleground. Casey Hayes sent him back into the fray one more time, and he ran second to Greek Song in the Dwyer Stakes. The Chenery colt was then given two months off.

When Hill Prince returned to the races at the end of August he was back in winning form. First he won the American Derby by a length and a half from All Blue and Your Host. Then he avenged his Dwyer Stakes loss by beating Greek Ship by four lengths in the Jerome Handicap. Middleground ran out of the money.

Hill Prince met only four others when he went to post for the Jockey Club Gold Cup. The small field included world record holder Noor, who had successfully conquered Citation, as well as the good mare Adile, winner of the Empire City Gold Cup and the Alabama Stakes. Hill Prince jumped to the lead immediately, and steadily increased it throughout the two mile race, winning by four lengths. Noor could do no better than second, although he beat Adile by seven lengths.

In the Thanksgiving Day Handicap at Hollywood Park, Hill Prince broke poorly, then ran out of ground in his closing drive, finishing just a head shy of Your Host and Ponder in a three-way photo finish. He was third again in the Hollywood Gold Cup. Blocked until too late, he nonetheless made a game effort and finished third behind Noor and Palestinian.

Hill Prince made up for the two defeats to win the Sunset Handicap from the champion mare Next Move while giving her fourteen pounds.

For his successes that season, Hill Prince was rewarded with the Horse of the Year title, as well as divisional championship honors.

Due to a fissure fracture in his right hind cannon bone, Hill Prince did not race until September of 1951. Then, he ran third behind the champion Tea-Maker while giving him weight in an overnight handicap, won an allowance race from the champion sprinter Sheila's Reward, and carried 128 pounds to a five length victory in the New York Handicap.

In the Jockey Club Gold Cup, Hill Prince was second by a head, caught at the wire by eventual Horse of the Year Counterpoint. He was second to Counterpoint again in the Empire City Gold Cup. Even with only two victories, the five length score in the New York Handicap was impressive enough to earn year end honors for Hill Prince. He was named co-champion handicap horse, sharing the honor with Citation, who had recently become the first equine millionaire.

Hill Prince raced only twice at five, beating his stablemate Bryan G. in the San Marcos Handicap and running fifth in the Santa Anita Handicap. He was then retired to stud.

Hill Prince, standing at Claiborne Farm, sired Bayou, the Champion Three Year Old Filly of 1957 and dam of classic producer Alluvial, and was the broodmare sire of Hall of Fame members Dark Mirage and Shuvee. Pensioned in 1969, Hill Prince returned to The Meadow, where he passed away after suffering a heart attack in 1970.

Elected to the Hall of Fame in 1991, he was ranked seventy-fifth on the century end poll printed by Blood-Horse.