Twenty Grand (KY)

Bred and raced by Helen Hay Whitney’s Greentree Stable, Twenty Grand was Horse of the Year in 1931 when he won eight major stakes races, including the Kentucky Derby and Belmont Stakes.

Painting of Twenty Grand by Richard Stone Reeves





St. Germans




All Gold


Greentree Stable


Greentree Stable


Thomas W. Murphy
James G. Rowe, Jr.
William Brennan
Cecil Boyd-Rochfort





Racing Record



Year Starts First Second Third Earnings
Year Sts 1 2 3 $
1930 8 4 2 1 $41380 $41,380
1931 10 8 1 1 $218545 $218,545
1932 2 1 1 0 $915 $915
1935 5 1 0 1 $950 $950


Bred and raced by Helen Hay Whitney’s Greentree Stable, Twenty Grand was Horse of the Year in 1931 when he won eight major stakes races, including the Kentucky Derby and Belmont Stakes.

Twenty Grand was in the first crop foaled and raised at the Kentucky farm purchased by Whitney in 1925. Trotting horseman Tom Murphy trained Twenty Grand as a juvenile. The bay son of St. Germans broke his maiden in his career debut, winning a five-furlong contest at Jamaica by five lengths on April 30, 1930. In his subsequent start, Twenty Grand finished second to Phantom Star and suffered bucked shins in the process. He returned to the races two months later and won an allowance at Aqueduct by three lengths.

Later in the campaign, Twenty Grand defeated Hall of Famer Equipoise in back-to-back showdowns in the Junior Champion Stakes and Kentucky Jockey Club Stakes, winning by one length and a nose, respectively. Twenty Grand’s time of 1:36 for one mile in the Kentucky Jockey Club was the best on record for a 2-year-old at the distance. Equipoise, however, turned the tables and defeated Twenty Grand in the Pimlico Futurity by a half-length. Twenty Grand concluded his 2-year-old season with wins in half of his eight starts. Murphy resigned as Greentree’s trainer at the end of the year and offered Whitney $125,000 for Twenty Grand on behalf of a syndicate; the offer was not seriously entertained and Twenty Grand passed into the care of trainer James G. Rowe, Jr.

As a 3-year-old in 1931, Twenty Grand opened with a victory in the Wood Memorial before advancing to the Triple Crown series. The Preakness was contested prior to the Kentucky Derby and Twenty Grand suffered an unfortunate defeat. He was badly bumped and knocked off stride at the clubhouse turn. Although he rallied in the stretch, Twenty Grand finished second to Mate by 1½ lengths. A week later, Twenty Grand won the Derby by four lengths in track-record time of 2:01⅘. Mate finished third. A month later, Twenty Grand won the Belmont by 10 lengths in stakes-record time of 2:29⅗.

Following the Belmont, Twenty Grand won the Dwyer Stakes before finishing third in the Arlington Classic. It was reported that Twenty Grand had suffered a back injury in the Dwyer and he was subsequently shelved for five weeks.

Arriving at Saratoga to contest the Travers, Twenty Grand was back in top form, winning the Midsummer Derby by 1¾ lengths. Next up was the 1¾-mile Saratoga Cup and a showdown with Sun Beau, having his best year as the world’s greatest money earner. The race was no contest, as Twenty Grand romped home a 10-length winner.

Twenty Grand then won the Lawrence Realization by six lengths and was sent off at odds of 1-50 for the two-mile Jockey Club Gold Cup — which he won with ease — in his final start of the year. Twenty Grand, however, struck his left front pastern in the race and suffered significant nerve damage.

Rowe died in the fall of 1931 and Twenty Grand passed into the care of William Brennan, who spent considerable time trying to get him back to the races. Twenty Grand returned in the fall of 1932 but was no longer a standout racehorse. He won an allowance and finished second in a minor handicap before being retired to stud.

When he proved sterile, Twenty Grand was brought back to the track as a 7-year-old in 1935. He won once in five starts (via a disqualification) and was no factor in finishing 10th in the inaugural Santa Anita Handicap. It was thought a change in climate might do something for Twenty Grand and he was shipped to England in the care of Capt. Cecil Boyd-Rochfort, but he was not a factor in two starts abroad.

Twenty Grand was retired for good with a career record of 14-4-3 from 25 starts and earnings of $261,790. He spent some time at King Ranch in Texas before returning home to Greentree. Twenty Grand died at the age of 20 on March 2, 1948.


Horse of the Year — 1931
Champion 3-Year-Old Male — 1931

Triple Crown Highlights

Won the Kentucky Derby — 1931
Won the Belmont Stakes — 1931


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