He was part of the 1928 crop which was considered by most Turf historians as one of the best ever. His contemporaries included Champions Equipoise, Jamestown, Mate and Vander Pool. He was the first homebred Classic winner foaled at Payne Whitney’s Greentree Stud.
The Whitney Family needs little introduction as thoroughbred owners and breeders. William Collins Whitney was the originator of the family fortune in the heady days of Wall Street stock speculation and devoted much of his energies to both government service and thoroughbred racing. Though not necessarily in that order. His two sons, William P. Whitney ( known as Payne) and Harry P. Whitney were the products of his first marriage to Flora Payne, the sister of the largest stockholder in the Standard Oil Company.
Greentree Stud owed its existence to the familial strife engendered by the hasty remarriage of William Collins Whitney after the death of his first wife. Whitney rewarded Harry with over half of his estate for his son's unabashed support for this second marriage. On the other hand his other son, Payne had actively opposed the remarriage. For this principled stand, he would receive less than a tenth of his father's estate and had become so estranged from the family that he was not even present when his father passed away.
Ultimately Payne would benefit from the estate of his uncle, Oliver Payne, who felt that Whitney's remarriage was a slight to his sister and rewarded his nephew with a bequest of 50 million dollars that did much to ease the inequity in inheritances and helped reconcile the brothers. While Payne was not initially very enthusiastic about thoroughbred racing and kept his memberships in both the Jockey Club and the Westchester Racing Association mainly for business and social purposes, it would be his wife, Helen Hay Whitney, who would be the driving force behind the establishment of Greentree Stud as one of the premier racing stables in America. Indeed Payne would always say fondly that his primary role in thoroughbred racing was as the manager of his wife's stables.
Helen Hay Whitney came from a prominent political family. Her father had been one of Abraham Lincoln's devoted personal secretaries. Later he would become Ambassador to Great Britain and then Secretary of State in the administrations of both William McKinley and Teddy Roosevelt. Much of Mrs. Whitney's initial foray into thoroughbred racing involved steeplechasing.
Payne had established a breeding venture in New Jersey in 1914 under the auspices of Greentree, a name derived from the luxurious Whitney estate on Long Island. By the early 1920's most operations had been transferred to the farm purchased in Kentucky that was adjacent to his brother's Whitney Stud. It was here that their first homebred Classic winner Twenty Grand was foaled.
His sire St. Germans was a top tier stayer who finished second to Sansovino in the English Derby. He accounted for several stakes in England, including the Doncaster Cup at 18 furlongs. Payne Whitney purchased him in 1925 for the eye catching sum of $125,000. In America, St. Germans led the Sire's List in 1931 the year his son, Twenty Grand dominated in the Derby and Belmont.
His dam Bonus was not much of a runner only managing to eke out 2 wins in 23 starts. But she came from a good family being a grand daughter of the mighty Persimmon out of Remembrance by Hamburg.
Twenty Grand made his first appearance in a maiden at Jamaica on April 30, 1930 a winning one prevailing by five lengths. He lost his next race and bucked his shins in the process. He was put away for three months and then won his return engagement in September.
After a surprising loss in the Babylon Handicap Twenty Grand found himself facing one of the stars of the crop, Equipoise, in his next two starts. In the Junior Champion, Twenty Grand, who had an eleven pound pull in the weights, defeated Equipoise by a length.
On October 30, the two would meet again. This time at equal weights in the Kentucky Jockey Club Stakes. It would be a race for the ages. Don Leon broke the fastest out of the gate, but Equipoise soon joined him and was winging his way in front three lengths to the good. Kurtsinger got Twenty Grand untangled from the pack and was picking off horses until he had Equipoise in his sights.
Twenty Grand caught him and poked his head in front. But Equipoise wasn’t through yet. Inch by inch he fought back and now they were running in tandem down the stretch. Both horses were all out and the crowd was on its feet shouting. At the end it was Twenty Grand prevailing by a short nostril and running the fastest mile ever by a two year old.
Equipoise would turn the tables on him in the Pimlico Futurity. Twenty Grand would also lose his final race that year to a new rival, Mate. His record for the year would be four wins out of eight starts. He proved to be a good, or even a very good horse as a two year old. But he wasn’t great, at least not yet. That would come shortly as a three year old.
Twenty Grand won his first outing, the Wood Memorial, in 1931. Again the Preakness came before the Kentucky Derby this year. It wouldn’t be until the following year, that the familiar race order of the American Classics was settled.
The Preakness would show case the three rivals: Twenty Grand, Equipoise and Mate. Twenty Grand would be bumped throughout the race, but once free of interference at the top of the stretch, he was closing gamely on Mate but fell short by 1 1/2 lengths. Equipoise could do no better than fourth that day.
The Kentucky Derby a week later looked like a rematch among the three rivals, but Equipoise was scratched the morning of the race due to a quarter crack that would force his retirement for the year. Twenty Grand came thundering down the stretch winning by four lengths and shaving over 1 and 2/5 seconds off the track record that day. Mate finished fourth.
Next up was the Belmont Stakes where Twenty Grand romped home by ten lengths over only two other challengers. One of whom was Jamestown, last year’s co-two year old champion.
Twenty Grand would have six more starts that year accounting for the Dwyer, Travers, Lawrence Realization, Jockey Club Gold Cup and the Saratoga Cup. His only loss would be to Mate in the Arlington Classic after wrenching his back in his prior start.
In the Saratoga Cup he annihilated Champion Handicapper Sun Beau who was at the top of his game that year; leaving the all-time leading money winner in the dust by over ten lengths. Twenty Grand was backed down to 1-50 in the Jockey Club Gold Cup and won as he pleased. But he whacked his left pastern during the race. The tendon filled affecting the splint bone and deadening the nerve.
Twenty Grand had 10 starts and eight wins as a three year old. He was named the 1931 Horse of the Year and the 1931 Champion Three Year Old.
There was an attempt to get the horse ready for a four year old season, but the lameness reoccurred and Twenty Grand was not the same horse. He was all out to beat an indifferent field in an allowance at Belmont. After one more nondescript race over a nondescript group of horses, Twenty Grand was retired.
He proved sterile at stud and was brought back to the races at seven. Battling reoccurring injuries, he started three times winning only once by disqualification over his equally crippled competitor, Equipoise.
In the inaugural running of the Santa Anita Handicap, the three great rivals: Twenty Grand, Equipoise and Mate would meet for the final time. Running on fumes, Mate finished sixth, Equipoise just behind him in seventh and Twenty Grand a distant tenth.
Thinking a change of scene might help, Twenty Grand was sent to England where after two starts he broke down completely and was returned to the States and Greentree Stud. He lived out his days in what was humorously known as the Gas House Gang comprised of steeplechasers: Easter Hero and Jolly Roger and handicapper Cherry Pie.
Twenty Grand’s final record shows: 25 starts 14 wins 4 seconds 3 thirds with earnings of $261,790. He was inducted into the Hall of Fame in 1957 in the same class as Equipoise. On the Blood Horse List of 100 Top American Horses, he comes in at number 52.
Blood Horse Editor Joe Estes once wrote that “there was magic in the name of Greentree’s Twenty Grand.” In an outstanding crop he was a good two year old, but a phenomenal three year old. 1931 was his year without any doubt. After that, chronic injuries stilled his greatness. Once retired, he became a marketing bonanza with everything from cars to cigarettes named after him. Without a doubt there was magic in his name.