Whirlaway was a psychotic horse, prone to wild adventurous trips around the racetrack. He was considered a mentally impaired horse who, intentionally or not, could be a danger to himself and those around him. But there was little question as to whether it was worth the effort to train him. In his three- and four-year-old seasons, he ran 42 times, winning 25, finishing second 13 times, and third on the other four occasions. Thanks to the patient handling of Ben Jones, Whirlaway became the first of eight Kentucky Derby winners and two Triple Crown winners for Calumet Farm.

The son of *Blenheim II flashed some of his brilliance as a two-year-old, winning seven starts, including four stakes races. His juvenile record is vastly superior to the previous four Triple Crown winners, who won a combined six races at two. But Whirlaway also lost nine times at two, and displayed a tendency for erratic behavior, frequently bearing out in the stretch, and even taking jockey Johnny Longden to the outside rail on the far turn of the Saratoga Special before coming on in the closing yards to win the race.

At the start of his sophomore campaign, Whirlaway was still exhibiting crazy behavior, and losses in both the Blue Grass Stakes and the Derby Trial left racing fans wondering just how good Whirlaway could be if he could clean up his act.

The racing world found out on May 3, 1941. For the Kentucky Derby, Jones had fitted Whirlaway with a new blinker, cutting away the blinker portion on the left side to give the colt clear vision on the left side but not on the right. He also made a riding change, replacing Wendall Eads with Eddie Arcaro. Arcaro, who had ridden Jones's first Kentucky Derby winner, Lawrin, three years earlier, had the tactical sense and gentle hands Jones was looking for. On Derby day, Whirlaway displayed his customary tendency to run near the back of the pack early on. With a quarter-mile left, Whirlaway had moved up to fourth place and was flying. And with the colt clicking off a final quarter of :23-4/5, the victory was his by eight lengths.

Despite walking out of the gate and trailing by nine lengths a half-mile into the May 10 Preakness Stakes, Whirlaway again came on late, this time winning by 5-1/2 lengths. Nearly a month later, in the Belmont Stakes, Whirlaway stunned the other three horses in the race by taking off after a half-mile, opening up a seven-length lead after six furlongs. Despite coming out a bit wide in the stretch, he won by 2-1/2 lengths to become the fifth Triple Crown winner.

The colt's brilliance was sustained from that point on all the way to the end of the 1942 season, when he was named Horse of the Year for the second straight time. By the time his four-year-old season ended, he had become the first Thoroughbred to earn $500,000 in career earnings--Calumet's other Triple Crown winner, Citation, would become racing's first millionaire nine years later--but he also became the third Triple Crown winner to fail in a match race. This time the race was run at Narragansett race track in Rhode Island, and the vanquisher was a talented three-year-old named Alsab who had been the leading two-year-old of 1941 and won the Preakness Stakes in `42. The 1-3/16-mile race featured an epic stretch duel, in which Alsab had practically all of a two-length lead erased before winning by the barest of noses.

Whirlaway returned to the races at five but ran poorly in a pair of starts and was retired after finishing fifth in the Equipoise Mile at Arlington, his first off-the-board finish since his two-year-old season. Whirlaway enjoyed some initial success at stud, but was never the first-choice stallion at Calumet, that honor falling to Bull Lea. Sold to French breeding interests, Whirlaway died in the southern Normandy region of France on April 6, 1953, just ten minutes after being bred to a mare.

Career Record Year Starts 1st 2nd 3rd Earnings
1940 16 7 2 4 $77,275
1941 20 13 5 2 $272,386
1942 22 12 8 2 $211,250
1943 2 0 0 1 $250
Career 60 32 15 9 $561,161

1940

1st--Saratoga Special
1st--Hopeful Stakes
1st--Breeders' Futurity
1st--Walden Stakes
2nd--United States Hotel Stakes
2nd--Grand Union Hotel Stakes
3rd--Arlington Futurity
3rd--Belmont Futurity
3rd--Pimlico Futurity

1941

1st--Kentucky Derby
1st--Preakness Stakes
1st--Belmont Stakes
1st--Saranac Handicap
1st--Travers Stakes
1st--American Derby
1st--Lawrence Realization
1st--Dwyer Stakes
2nd--Jockey Club Gold Cup
2nd--Blue Grass Stakes
2nd--Derby Trial
2nd--Classic Stakes
2nd--Narragansett Special

1942

1st--Clark Handicap
1st--Dixie Handicap
1st--Brooklyn Handicap
1st--Massachusetts Handicap
1st--Trenton Handicap
1st--Narragansett Special
1st--Jockey Club Gold Cup
1st--Washington Handicap
1st--Governor Bowie Handicap
1st--Louisiana Handicap
2nd--Phoenix Handicap
2nd--Suburban Handicap
2nd--Butler Handicap
2nd--Arlington Handicap
2nd--match race with Alsab
2nd--Manhattan Handicap
2nd--Riggs Handicap
3rd--Carter Handicap
3rd--New York Handicap