Owned and bred by Helen Hay Whitney's Greentree Stable, Twenty Grand was a bay colt by St. Germans out of Bonus.
Trained at age three by James G. Rowe, Jr. and ridden by jockey Charley Kurtsinger, Twenty Grand raced against very strong opponents in 1930 and 1931 when he was part of what the Chicago Tribune newspaper called the "big four" in racing, which included Jamestown, Mate, and Equipoise.
In his only blemish of the year, Twenty Grand just missed the Triple Crown, finishing second to Mate in the Preakness.
As Twenty Grand tried to pass the leaders on the clubhouse turn, he was bumped badly by Clock Tower.
His jockey, Charlie Kurtsinger, chose the rail and went inside, but the tiring Mate blocked Twenty Grand and held on to win by a half length.