On his bare record, Whirlaway was a very good horse but not great because he lost nearly half his races. However, the qualities that made Whirlaway great and that endeared him to the racing public were not those of consistency but of great ability combined with a wayward streak. Jimmy Jones, son of the colt's trainer, recalled that "Whirlaway was a creature of habit. You had to create habits for him. So we created the habits we wanted him to do." [Keeneland Magazine, Oct. 1998]
The champion colt had a habit of bearing out, drifting toward the middle of the racetrack, during the latter part of his races and getting himself beaten. In preparing Whirlaway for the Kentucky Derby, this had been such a problem that trainer Ben A. Jones fitted the colt with a full-cup blinker over his right eye, and then in the colt's final work before the Derby, he cut a small hole in the blinker so that Whirlaway had a tiny field of vision, positioned himself ten feet off the inner rail, and told jockey Eddie Arcaro to ride the horse through that space. Whirlaway was able to see his trainer, Arcaro was able to keep him on a straight path, and Whirlaway won the Kentucky Derby.
Trained by Ben A. Jones and ridden by Arcaro, Whirlaway won the U.S. Triple Crown in 1941. He also won the Lawrence Realization Stakes and the Travers Stakes that year. He was voted the Horse of the Year for 1941 and repeated as Horse of the Year in 1942.
Arcaro was the sole rider for Whirlaway in all his 3-year-old victories, yet was forced to stand down for the 1942 season due to racing infractions that resulted in a year-long suspension.  Jockey George Woolf took the reins for most of the 1942 season.
Woolf, who had previously won the Pimlico Special in 1938 on Seabiscuit and in 1940 on Challedon, rode this 1941 Triple Crown winner at a leisurely pace during the 1942 Pimlico Special in a walkover victory. No opponent had been found to challenge Whirlaway for the race. On December 12, more than twenty thousand people turned out to watch Whirlaway win the inaugural Louisiana Handicap at the Fair Grounds Race Course. The newly formed Thoroughbred Racing Association staged this event as a war relief effort.
Whirlaway entered stud at Calumet Farm in the spring of 1944 at age six, and among his best offspring were Scattered (winner of the Coaching Club American Oaks), Whirl Some (Selima Stakes), and Dart By (All American Handicap). In August 1950, Calumet Farm leased Whirlaway to French breeder Marcel Boussac, who stood Whirlaway at his breeding farm, Haras de Fresnay-le-Buffard. Boussac purchased Whirlaway from Calumet in September 1952 [Thoroughbred Record 27September1952], and the horse died at Boussac's French stud in 1953 [Thoroughbred Record 11April1953].
Whirlaway was elected to the National Museum of Racing and Hall of Fame in 1959. In The Blood-Horse magazine's ranking of the top 100 U.S. thoroughbred champions of the 20th Century, Whirlaway was No. 26.
- Every horse that has ever participated in a classic: Kentucky Derby, Preakness, or Belmont
- Whirlway's Triple Crown History