Triple Crown profile: Whirlaway

The Kentucky Derby has been postponed until September, but Churchill Downs will still celebrate the first Saturday in May with a nationwide virtual "Kentucky Derby at Home" party. This special, day-long event will aim to raise $2 million for COVID-19 emergency relief efforts and will feature a thrilling simulated race that includes the 13 Triple Crown winners.

To get you ready for the virtual race, BetAmerica is publishing a profile on each Triple Crown winner leading up to the big day. Get ready to travel back in time to some of the greatest moments in Thoroughbred racing history.

Whirlaway (1941)

Owner: Calumet Farm

Trainer: Ben Jones

Jockey: Eddie Arcaro  

Before the Derby

Whirlaway was born at Calumet Farm on April 2, 1938. His sire was Blenheim II, winner of Britain’s prestigious Derby Stakes in 1930 and sire of 1935 Derby Stakes winner Mahmoud. Blenheim II was purchased by a U.S. syndicate in 1936, and Whirlaway was part of his first American crop.

Whirlaway’s dam was Dustwhirl, an unraced daughter of 1910 Belmont Stakes winner Sweep, who produced five winners aside from the 1941 Triple Crown champion in her lifetime. She was purchased from Claiborne Farm for $12,000 while in foal to Whirlaway.

Whirlaway was trained by Hall of Famer Ben A. Jones, who had already claimed one of his six Kentucky Derby victories in 1938 with Lawrin, but the Blenheim II colt was anything but the apple of his eye. Whirlaway was “the dumbest horse I ever trained,” Jones once said.

The colt was high strung, with bizarre tendencies. He nearly missed victory on debut in June of 1940 because he bore out so badly.

In his sixth start, Whirlaway was equipped with blinkers, which he wore for almost every subsequent race. Jones eventually supplied Whirlaway with blinkers that almost completely covered his right eye, so he wouldn’t bear out like he did when he won the Hopeful at Saratoga.

Another distinguishing characteristic of Whirlaway was his extremely long tail, which was kept that way by Jones to discourage opponents from getting too close to his energetic colt on the track. The nickname “Mr. Longtail” followed Whirlaway throughout his career.

Whirlaway started 16 times at 2 and was a seven-time winner, but he was defeated handily by Our Boots in the Belmont Futurity. Although “Whirly” was dubbed Turf & Sports Digest’s 2-year-old of the year, the Daily Racing Form’s coveted award went to Our Boots.

The Derby

Whirlaway began his 1941 campaign with three wins in five sprint races, then checked in second in the Blue Grass behind Our Boots at Keeneland. Five days later, Whirlaway finished second again in Churchill Downs’ Derby Trial.

With the Kentucky Derby less than four days away, Jones decided to make a jockey change on Whirlaway, from Wendell Eads (who admitted in later years that he was “not strong enough” to ride the headstrong colt) to Eddie Arcaro. Arcaro rode Lawrin to his Derby victory, but the rider had only one chance to get to know Whirlaway, in a workout before the big race.

Whirlaway went off a tepid favorite (2.90-1) in an 11-horse field, over Our Boots (3.90-1) and Santa Anita Derby winner Porter’s Cap (3.30-1).

He was blocked early, but Whirlaway was soon guided to the clear by Arcaro and gradually made his way to fourth by the quarter pole. Arcaro drove Whirlaway between longshots Staretor and Market King and the colt surged home to win by a record-tying eight lengths. His final time of 2:01 2/5 stood as a Kentucky Derby record until 1962.

Completing the Triple Crown

Just a week after his emphatic Derby victory, Whirlaway was back in action for the Preakness. The 1.15-1 favorite was last of eight early, because of a slow break from the gate, but assumed a five-length lead by the quarter pole and won by 5 1/2 lengths. Our Boots took another stab at “Whirly” in the Preakness but could only manage third.

Ten days later, Whirlaway beat older horses in a 1 1/16-mile allowance at Belmont Park. Two and a half weeks after that, he raced his way into the history books with a victory in the Belmont Stakes.

The 1941 Belmont was a breeze for Whirlaway, who scared off all but three challengers. He was in third place at first call but soon took over and galloped home a 2 1/2-length victor as the 1-4 favorite.

After the Triple Crown

Whirlaway won six more races during his 3-year-old season, including the Travers at Saratoga. He is the only horse to ever win the Triple Crown and the Travers. DRF named Whirlaway 1941’s Horse of the Year.

The following year, Whirlaway gained a worthy adversary in Alsab, 1941’s juvenile male champion and 1942’s 3-year-old male champ. While "Mr. Longtail" was busy beating handicap horses in the Clark, Dixie, Brooklyn, and Massachusetts (the race that helped him eclipse Seabiscuit’s all-time earnings record), Alsab compiled victories in the Preakness, Dwyer, and American Derby (he also finished second in the Kentucky Derby and Belmont).

The two finally collided in a match race at Narragansett Park on Sept. 19, 1942, and Alsab held off Whirlaway by a nose in a dramatic stretch run. On Oct. 3, the pair met again in the Jockey Club Gold Cup at Belmont, where Whirlaway emerged victorious. One week later, Alsab turned the tables again by beating Whirlaway in the New York Handicap.

Whirlaway won four of his final five starts in 1942, including his walkover score in the Pimlico Special. "Whirly" attempted to defend his 1942 Horse of the Year crown in 1943 but pulled up sore in the Equipoise Mile in June and was retired to stud with a record of 32-15-9 and earnings of $561,161 from 60 starts. 

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Tune into Churchill Downs’ virtual ‘Kentucky Derby at Home’ party on NBC on May 2 from 3:00 to 6:00 p.m. EDT