By the time the Kentucky Derby of 1920 rolled along, Man o' War was acknowledged as a fierce competitor, and everyone was afraid to race their own horses against the Big Red, as he was known. However, Big Red did not run in the Kentucky Derby. Samuel Riddle, his owner, believed that May was too early for three-year-old horses to race. Consequently, seventeen horses ran the Derby in his absence.
The next week, only a handful of Derby entrants had the guts to run against Big Red in the Preakness at Pimlico Park in Baltimore. It would be 1 3/16 miles long, quite a distance for young horses. Nevertheless, Big Red took and early lead, fending Upset off in the homestretch and winning by 1 1/2 lengths. He ran a fast time of 1:51.3 seconds.
Next came the Withers Stakes. Only two horses raced against Man o' War, who was only carrying 118 pounds in the mile long race. He won easily, beating the second-placer, Wildair, by two lengths, and setting a new American record of 1:35 4/5.
Then he ran in the Belmont Stakes(1 3/8 miles), which was pretty much a match race between him and Donnacona, the only horse who accepted the challenge. Both horses carried 126 pounds. Even so, Big Red easily drew away from Donnacona, breaking Sir Barton's American record by over three seconds with a time of 2:14 1/5. This made his time a new world record! In addition, he beat Donnacona by 20 lengths!
Undoubtedly, Man o' War was the greatest racehorse of his time. Every racing fan had no doubt that he would succeed in his next race, the Stuyvesant Handicap. They would just have to wait and see.