Ironically, another foal who shared the same markings had born around the same time. Trainer Ben Jones and his son JImmy had a hard time telling the two apart until they finally began training.
Jimmy claimed that Whirlaway "gave the impression of being tireless, able to gallop all day if we didn't stop him." Unfortunately, with his gift of stamina came a rather unpleasant trait: he had trouble running in a strait line, and would zigzag around the track when he was in the lead. Consequently, he barely won his first, which took place on June 3, 1940, though he was the superior horse.
Whirlaway was not only the most promising colt that year horse, but also the most difficult to train. Because of this, Ben Jones focused his attention on Whirlaway while his son trained the other horses.
|Whirlaway standing beside|
Ben Jones, his trainer(photo credit).
In the Saratoga Special, when Whirlaway was continue his usual zigzags, he crashed into the outer rail, winning despite his injuries.
Ben Jones called Whirlaway the dumbest horse he had trained, but he knew that he was also the fastest, so he spent time with the horse to break him of his bad habits. Even turf write Bill Corum had faith in The Flying Tail(name for his bushy tail), and predicted the he would win that year's Hopeful and Futurity Stakes, as well as the next year's Triple Crown.
True the prediction, Whirlaway won the Hopeful Stakes, but not with out injury. While on the track, a piece of debris flew into his eye, yet he continued despite the injury, proving that he had the heart to win.
However, he had to leave the track for two months while veterinarians and eye specialists treated the eye, finally managing to save it. Once he had returned, he won the Breeders' Futurity in Keeneland, followed by the Walden Stakes at Pimlico.
By that time, he had become the season's top money winner, and shared the title of Two-year-old Champion with Our Boots.