Whirlaway was the fifth winner of the U.S Triple Crown races. He was a chestnut stallion sired by English Derby winner Blenheim II. He was foaled at Calumet Farm in Lexington, Kentucky. His trainer was Ben A. Jones. Many fans gave their favorite horses affectionate nicknames, and Whirlaway was dubbed Mr. Longtail or The Flying Tail. This was probably a result of his luxuriously long, unracehorse like tail.
Whirlaway started his racing career on June 3, 1940 with a narrow victory in Chicago. His regular jockey was Eddie Arcaro.
At the 1941 Kentucky Derby he took off at the top of the homestretch to make an eight length victory. His time of 2:01 2/5 set the new track record which stood for more than twenty years. During the Preakness Stakes he Whirlaway almost walked out of the starting gate and was so much farther behind all the other horses. Then on the backstretch he and jockey Eddie Arcaro flew by all he other horses and won by five and a half lengths. At the Belmont Stakes he has scared away most of the competition, leaving only a field of four. He won, but in a slow 2:31. That completed his U.S Triple Crown win.
That year Whirlaway continued to win during the 1941 season. Winning the Dwyer then the American Derby in Chicago, and then continuing his winning streak by winning the Travers Stakes. after that he won the Saranac Handicap, then the Lawrence Realization. But then at the Jockey Club Gold Cup he lost in a hard fight for the win. Near the end of the 1941 season Whirlaway and some other Calumet Farm horses were shipped to Santa Anita for the upcoming winter races. But the bombing of Pearl Harbor brought all racing on the West Coast to an immediate halt. And World War II travel restrictions prevented them from going back east until March. But Whirlaway was still named the 1941 Colt of The Year and Champion Three Year Old Colt.
Whirlaway had a very successful racing season as a four year-old. During the whole 1942 season he never finished out of the money. He returned to Churchill Downs to win the Clark Handicap, and then he won the Dixie Handicap. After that he won the Garden State Stakes and the Narragansett Special. But then Whirlaway’s winning streak came to an end when he finished second by only the tip of bay colt Alsab’s nostril. Alsab had been getting a lot of attention recently after winning the Preakness and nine other races, but when they met again at the Jockey Club Gold Cup Whirlaway beat Alsab by three-quarters a length. After that victory he went on to win the Washington Handicap and the Governor Bowie Stakes. Then he won the Pimlico Special in a walkover. To finish the season he won the Louisiana Handicap, but bowed a tendon in doing so.
In the spring of 1944 at age six he stood as stud at Calumet Farm. He had a successful breeding career and sired many horses, including stakes winner Rock Drill. Then in August 1950 Calumet leased him to French breeder Marcel Boussac who stood him at his breeding farm Haras de Fresnay-le-Buffard. Then Boussac loving Whirlaway fully purchased him from Calumet in September 1952. But in 1953 Whirlaway died from a nerve tissue rupture.
Whirlaway had a very successful racing career, his ending record was 60 starts: 32 wins, 15 seconds, and 9 thirds. He only finished out of the money four times. His total earnings were $561,161 for his whole career. And in 1959 he was elected to the National Museum of Racing and Hall of Fame. Also he was ranked #26 on the Blood-Horse magazines ranking of the top 100 US thoroughbred champions of the 20th century.