There is no question about it, Whirlaway was a psychopath as far as horses went. He was quite prone to some wild adventurous trips around a race track. He was actually considered a mentally ill horse, however that is actually determined. He was a danger to himself and those around him. But there was no doubt in Ben Jones' mind that this horse was worth training. In his 3 and 4 year old seasons he ran 42 races, winning 25 of them and finishing second 13 times. Truly amazing for a horse that old. Whirlaway became the first of 8 Kentucky Derby winners and the first of 2 triple crown winners for Calumet Farm.
Whirlaway was the son of Blenheim II. In his 2 year old season he did show some signs of brilliance. He won seven starts which included four stakes races. His early record was actually much better than any other previous triple crown winner. All of them combined only won six races by the age of two. But Whirlaway also lost 9 times that year and began to show signs of very erratic behavior. Many times he would run a race and take his jockey to the outside rail before coming back inside and moving in for the kill. He was a very difficult horse to control because of his mental problems.
At the start of his second year of racing, Whirlaway was still showing signs of extremely erratic behavior and it was feared that he would never be ready for the really big races. He lost his first two races that year and fans were left wondering if he would ever be the great horse that Calumet Farm said he would be.
Well, the fans and the rest of the racing world didn't have to wait long. On May 3, 1941, Whirlaway ran in the Kentucky Derby. Jones had made some modifications to Whirlaway's blinker so that he could see a little better on the left side but not on the right. He also put Eddie Arcaro on Whirlaway, replacing his old jockey Wendall Eads. Arcaro had ridden a previous Kentucky Derby winner of Jones'. When the race started, Whirlaway did his usual bit of staying at the back of the pack. But with just a quarter mile left, Whirlaway took off and left the others in the dust, winning by 8 lengths.
The Preakness was no different. At one point, Whirlaway was trailing by 9 lengths and it appeared that he was out of the race. But again, he came on late and ended up winning the Preakness by 5 1/2 lengths.
Finally, a month later at the Belmont Stakes, Whirlaway notched up his place in racing history. This time he came out strong, building a 7 length lead. Even though he started to tire at the end he still hung on for a 2 1/2 length victory.
Sadly, after he retired and was sold to breed, he died just 10 minutes after being taken to a mare.
