"And there is magic in the name of Greentree's Twenty Grand," penned J.A. Estes. A bay son of the high priced import *St. Germans, Twenty Grand raced with one of the most talented crops of juveniles to run in America and rose to the top of his class as a three-year-old.

Twenty Grand raced for his breeder, Mrs. Payne Whitney, owner of Greentree Stable, and therefore was not named for his purchase price, as is often believed. Around Derby time, one possible source of the name was suggested. It was said that an offer of $20,000 had been made for the colt as a weanling, but whether the story was true is unknown.

As a juvenile, Twenty Grand was trained by Thomas W. Murphy. After breaking his maiden at first asking with a five length score at Jamaica, Twenty Grand bucked shins and missed three months of racing. He went to the post again at Empire City, running second, then got another two months off. In the meantime, Jamestown took five juvenile stakes, and retired for the year without meeting the Greentree runner.

Upon his return to the races in September, Twenty Grand scored in allowance company, but ran out of the money in the Babylon Handicap.

A week later, with Charles Kurtsinger in the irons for the first time, Twenty Grand met C.V. Whitney's star Equipoise for the first time, beating him by a length in the Junior Champion Stakes.

The pair met again in the Kentucky Jockey Club Stakes. In beating Equipoise by a nose, Twenty Grand clocked the fastest mile ever run by a two-year-old. When the two met for a third time in the Pimlico Futurity, it was called "The Most Spectacular Race of the Decade." Twenty Grand was battling with Mate for the lead when Equipoise stormed from behind just in time to score a victory, with Twenty Grand second. After running third behind Mate and Sweep All in the Walden Handicap, the Greentree star retired for the season, leaving Equipoise and Jamestown to share divisional honors.

James Rowe, Jr. took over training duties at Greentree in 1931. Twenty Grand began his sophomore year by scoring a half length victory over Clock Tower in the Wood Memorial. The Preakness was run only seven days later. Suffering interference, Twenty Grand was unable to catch Mate, and ran second.

Made the favorite at Churchill Downs, he easily scored a four length victory over Sweep All and Mate to set a new Churchill Downs record of 2:01 4/5. Twenty Grand then won the Belmont Stakes by an authoritative ten lengths.

In the Dwyer, the Greentree star soundly defeated Wheatley Stable's Blenheim, the colt responsible for the 'II' after the 1930 Epsom Derby winner's name, by two lengths.

Forced wide, Twenty Grand's fast finish wasn't enough to catch Mate before the wire in the Arlington Classic, but he wasn't beaten again that year.

Twenty Grand romped to victory in the Travers Stakes, beating St. Brideaux by a length and a half. In the Saratoga Cup, he handed defeat to the great money earner Sun Beau, beating the older star by ten lengths. In the Lawrence Realization he beat Sun Meadow by six lengths, covering the mile and five eighths in 2:41 1/5, just two-fifth's shy of Man o' War's track record.

In the final race of the season, Twenty Grand was injured while winning the Jockey Club Gold Cup by three lengths. Named Horse of the Year, he had earned $218,545, with eight victories in ten attempts.

After winning his season debut at four, Twenty Grand pulled up lame after running second in an overnight handicap at Laurel. He retired to stud at Greentree.

When he proved sterile, Twenty Grand was returned to the races at seven.

The Greentree runner ran third in an overnight, pulling up sore. After a month of rest, he beat Equipoise by disqualification in another handicap, then finished out of the money in the first running of the Santa Anita Handicap.

Twenty Grand was shipped across the Atlantic. Trainer Cecil Boyd-Rochfort was unable to win a race with him, and the horse was retired.

Twenty Grand lived out his days as a pensioner at Greentree Stud, where the Whitney pensioners, including Cherry Pie, Easter Hero, and the steeplechase hero Jolly Roger, were collectively called "The Gashouse Gang." Twenty Grand died March 2, 1948, and is buried on the farm. He became a member of the Hall of Fame in 1957.

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