Whirlaway (April 2, 1938 - April 6, 1953) was an American champion thoroughbred racehorse. The chestnut horse was sired by English Derby winner Blenheim II, out of the broodmare Dustwhirl. Whirlaway was bred at Calumet Farm in Lexington, Kentucky. Trained by Ben A. Jones and ridden by Arcaro, Whirlaway won the U.S. Triple Crown in 1941.
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." 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 preparations 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. In Whirlaway's final work before the Derby, Jones cut a small hole in the blinker so that the horse had a tiny field of vision. Jones then 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 in 1941, beating Alsab by 96 votes to 91 in a poll conducted by the Turf and Sport Digest magazine. A year later, Whirlaway repeated his win in the poll, beating Alsab with 76 votes to his rival's 45.
Arcaro was the sole rider for Whirlaway in all of his 3-year-old victories, but he stood down for most of the 1942 season due to racing infractions that resulted in a long suspension.  Jockey George Woolf took the reins for the majority of the 1942 season. On September 19, 1942, Alsab defeated the 1941 Triple Crown champion in a match race at Narragansett Park in Pawtucket, Rhode Island. Although Whirlaway closed strongly through the stretch, after racing wide throughout, it was Alsab going to the lead, having something left in the tank, and lasting by a nose as both horses flew home through the stretch run. Still, Whirlaway was named Horse of the Year for 1942 after defeating Alsab in a subsequent race and having 12 wins for the year to Alsab's 9.
Woolf, who had previously won the Pimlico Special in 1938 on Seabiscuit and in 1940 on Challedon, rode the 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. 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 the horse at his breeding farm, Haras de Fresnay-le-Buffard. Boussac purchased Whirlaway from Calumet in September 1952 [Thoroughbred Record 27 September 1952], and the horse died at Boussac's French stud in 1953 [Thoroughbred Record 11 April 1953].
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, he was No. 26.
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- "Whirlaway cops honor for year". Pittsburgh Post-Gazette. 1941-12-09. Retrieved 2012-02-27.
- "Whirlaway is again winner of Horse of Year Crown". Calgary Herald. 1942-12-16. Retrieved 2012-02-27.
- Lawrence Journal-World - September 21, 1942
- Whirlway's pedigree
- Whirlaway's Kentucky Derby
- Every horse that has ever participated in a classic: Kentucky Derby, Preakness, or Belmont
- Whirlway's Triple Crown History