Whirlaway was the son of Blenheim II, out of Dustwhirl, by Sweep. Whether his crazy acts were intentional or not, he was considered psychotic and a danger to himself and everyone around him. But there is little question as to whether it was worth the effort to train him.
As a two year old, Whirlaway won seven starts, including four stakes races. In his three and four-year old seasons he ran 42 times, winning 25 and placing second 13 times and third 4 times. But his crazy behavior left racing fans wondering just how good he could be if he cleaned up his act.
On May 1, 1941, Whirlaway entered the Kentucky Derby track with a customized set of blinkers. Trainer Ben Jones cut the left blinker in half so Whirlaway could only see the inside rail and not the outside. He also had a new jockey, Eddie Arcaro on board. Jones had Arcaro walk Whirlaway inside the rail before the race to get him used to the crowd.
When the gates opened, Whirlaway lagged behind the pack, but with only a quarter mile left he moved up to fourth. With an incredible burst of speed, Whirlaway shot to the front and charged to the wire, winning by 8 lengths.
In the Preakness Stakes on May 10, Whirlaway practically walked out of the gate. He trailed miserably but surprised the crowd by quickly closing the huge gap and weaving through the horses to win big by 5 1/2 lengths.
Nearly a month later he entered the Belmont Stakes with only three other horses taking him on. He had a seven length lead after six furlongs but lost ground when he went too wide on the turn. He won with only a 2 1/2 length lead and became the fifth Triple Crown Winner.
At the end of his 1942 season, Whirlaway took the Horse of the Year Award for the second straight time. And at the end of his four year old season, he was the first horse to earn $500,000 in career earnings. Nine years later, Citation would become racings first millionaire.
Whirlaway raced again as a five year old but ran poorly. He was retired after finishing fifth in the Equipoise Mile it Arlington. It was his first off-the-board finish since his two year old season. He enjoyed some initial success at stud and was later sold to French breeding interests. Whirlaway died on the southern Normandy region of France on April 6, 1953 at age 15, just ten minutes after being bred to a mare. He is considered the 26th best of the top 100 racehorses of the 20th century.