It's never a good thing when your boss calls you a knucklehead.

“You can teach him,” quipped legendary trainer Ben A. Jones of Whirlaway in the spring of 1941, “but you can't teach him much. ”

Exasperated by the colt's penchant for bolting out sharply on the stretch turn, Jones devised the "one-eye blinker" that shielded Whirlaway's right eye. Conducting a daring experiment with new jockey Eddie Arcaro in the irons, Jones was perched on his stable pony stationed 10 feet from the inner rail at the head of the stretch. Arcaro was instructed to pilot the flaming chestnut colt through the slim opening.

“I could see that old man just sitting there on his pony,” Arcaro said. “I was bearing down on him full tilt, and I was scared to death we'd have a collision that would kill the both of us. But B.A. [Jones] never moved a muscle, and Whirlaway slipped through there as pretty as you please. Then I knew we had a hell of a chance in the Derby.”

Undeterred by his zany behavior, the betting public sent Whirlaway off as the nearly 3-to-1 favorite in the 1941 Kentucky Derby. He trailed by 14 lengths down the backstretch. With his customized headgear and his new partner at the helm, Whirlaway flew down the stretch and crossed the wire eight lengths better than Staretor, clocked in a time of 2:01 2/5, a record that stood for 21 years. His final quarter (23 3/5 seconds) was only two-fifths of a second slower than Secretariat's remarkable effort in 1973.

A star was born.

Swift but temperamental, Whirlaway was Jones' private pupil. The trainer devoted countless hours to his colt, accompanying him, schooling him, working him, relaxing him. In the end, the flashy chestnut rewarded Jones' painstaking efforts by becoming racing’s fifth Triple Crown winner and Horse of the Year in 1941. Whirlaway repeated as Horse of the Year the following season.

“That was one of the greatest jobs of training I ever saw,” noted Jimmy Jones, the trainer's son. “He was a peculiar horse in that he had a very stubborn disposition, but he learned. He would respond to habit-building, and that's really what made the horse go.”

The sight of the small colt with the unusually lengthy and bushy tail — streaming like a pennant in his wake when he was in high gear — gave rise to his popular nickname, "Mr. Longtail." More often than not Mr. Longtail's sensational races landed him on the front pages of the nation's sports sections above Ted Williams, who batted .406 that year, and Joe DiMaggio, who put together a 56-game hitting streak.

At age 5, Whirlaway retired with a record of 32 wins, 15 seconds and nine thirds from 60 starts with a bankroll of $561,161, the all-time leading money earning Thoroughbred. He spent much of his 4-year old season running for war bonds, racing 22 times and raising $5 million. That only added to Whirlaway's stature as a national hero.

Owned and bred by Warren Wright's famed Calumet Farm, Whirlaway's breeding curiously foreshadowed his erratic behavior. He was from the first American-sired crop of the 1930 English Epsom Derby champion, Blenheim II. In that race, Blenheim II broke to his right and continued racing outside before unleashing a devastating turn of foot in deep stretch to pull away. Whirlaway's unraced dam, Dustwhirl, was a bundle of nerves and the daughter of highly touted sire Sweep, the broodmare sire of 1937 Triple Crown winner War Admiral. 

Whirlaway with his dam, Dustwhirl. (Keeneland-Thayer photo)

As a juvenile, Whirlaway displayed flashes of brilliance, winning seven times inclduing four in stakes races, but he also went down in defeat on nine occasions. He made a mess of the Pimlico Futurity careening wide on both turns and beaten by five lengths while finishing third.

The start of his 3-year-old campaign was just as inconsistent, with Whirlaway winning two allowance races and losing a pair at Hialeah Park in Florida. The colt's maddening antics returned in the Blue Grass Stakes when he bore out badly, resulting in a 6-length loss to his chief rival Our Boots. The willful colt pulled a similar stunt in the Derby Trial when he nullified his blistering move on the far turn by drifting to the far outside to wind up second by three-quarters of a length.

Jones had seen enough. The consummate horseman cleverly concocted an equipment change to Whirlaway's blinkers a day before the 67th Kentucky Derby. With his pocketknife Jones sliced away the cup on his left side leaving the right eye covered, reasoning that this would curtail his veering out. Another part of the equation was to book future Hall of Famer Eddie Arcaro as the rider.

Whirlaway wins the 1941 Kentucky Derby. (Blood-Horse Library photo)

Fitted with the one-eyed blinker, when Arcaro called on the colt to run rounding the far turn, Whirlaway took off. He romped home to an 8-length victory. It was the first of eight Derby winners for Calumet Farm. One week later, Whirlaway walked out of the gate in the Preakness Stakes trailing the next-to-last horse by six lengths headinig up the backstretch. When Arcaro shook the reins the colt circled the entire field by the quarter pole and, gearing down, he won by 5 1/2 lengths.

“Not even a cyclone could head us off,” said a jubilant Arcaro on his way to the winner's circle. “I don't think I ever passed as many horses in such a hurry. I might as well have been shot from a gun. What a horse! What a horse!”

That scintillating burst of speed scared away all but three rivals in the Belmont Stakes, the "Test of the Champion". The other riders set a dawdling early pace, but Arcaro wasn't duped. When they hit the half-mile pole, Acaro shouted at his rivals, "the hell with this fellas, I'm leaving."

Whirlaway seized the race and kept right on running to become Calumet Farm's first of two Triple Crown winners, the other Citation in 1948.

“He was so good he made ducks and drakes of his opposition,” wrote Bryan Field in the New York Times. “The chestnut colt from the Calumet Farm raced through the stretch so easily that he had his ears pricking, and he also had that mightiest Triple Crown tilted jauntily on his handsome forelock.”

Whirlaway with Wendall Eads up; Pinky Brown on white horse. (Keeneland Library-Cook)

Whirlaway went on to triumph in the Travers — the only Triple Crown winner to do so. He finished out the year with 13 wins in 20 starts, plus five seconds and two thirds. At age 4, racing secretaries piled on the weight, but Whirlaway hit the board in each of his starts, winning a dozen of 22 races with eight seconds and two thirds.

Whirlaway suffered a tendon injury late in 1942, and when he ran fifth in the Equipoise Mile at Arlington Park in June of 1943, that ended a 48-race streak of in-the-money finishes. Over a four-year career Whirlaway ran 60 times, at 17 tracks earning $561,161.

Epilogue

Whirlaway stood stud at Claiborne Farm, but his legacy was not as a sire. He sired 18 stakes winners, including Scattered, who won the 1948 Coaching Club American Oaks. His daughter Whirling Girl produced a Bull Lea filly named Girlea who in turn produced Lady Golconda, the dam of three time Horse of the Year Forego. 

In 1950, Whirlaway was leased for three years to Marcel Boussac, a French textile magnate who shipped the horse to stand at Haras Fresnay-le-Buffard in Normandy and later negotiated an outright purchase of the stallion. On April 6, 1953, at age 15, Whirlaway died suddenly of a rupture in his nerve tissue moments after he was bred to a mare. He was buried on the French farm near Normandy, not far from that famous war battlefield. His body was later returned to Kentucky, and he is now buried at Calumet. Whirlaway was enshrined in the Racing Hall of Fame in 1959.  

Editor's Note: This story was originally published in 2014 and has been updated.