October 21, 2020

Historical Cameo – Whirlaway

Whirlaway wins the 1941 Kentucky Derby
Whirlaway (Courtesy of the Kentucky Derby/Churchill Downs)

Whirlaway — 1941 Triple Crown winner

Originally appeared February 9, 2006. — In light of Aqueduct’s staging the Whirlaway Stakes, we commemorate the first all-time great campaigned by Calumet Farm and one of our sport’s most captivating personalities. The flaming chestnut was a real crowd-pleaser, thrilling spectators with explosive last-to-first bursts that became his trademark. The sight of the smallish colt with the unusually lengthy tail, streaming like a pennant in his wake when he was in high gear, gave rise to his popular nickname, “Mr. Longtail.” Whirlaway’s talent, however, came with a price: a maddening host of quirks that could have seriously compromised his racing career had he been in the hands of a horseman less gifted than Ben Jones. His story is a case study of the pivotal role of the trainer in the successful development of physically brilliant but mentally erratic horses.

Whirlaway had the genetic deck stacked against him when he drew his temperament card…

Whirlaway had the genetic deck stacked against him when he drew his temperament card, as both his sire and his dam had reputations for being excitable. His sire, *Blenheim II, was a dashing winner of the Derby at England’s famed Epsom racecourse, but his behavior in that race was a curious foreshadowing of Whirlaway’s antics. He broke to his right, spotting the field several lengths, then showed a distinct preference for racing on the far outside before delivering an amazing burst of acceleration in deep stretch to score. Mr. Longtail’s dam, Dustwhirl, was characterized as a nervous individual who never raced. She was nevertheless a daughter of the highly influential sire Sweep, who was also the broodmare sire of 1937 Triple Crown winner War Admiral.

Raw ability…

Hence Whirlaway inherited plenty of raw ability with a complimentary set of psychoses to match, and this heady cocktail was served up early in his two-year-old season. Frightened by many things in his environment, he was difficult to saddle, prone to rear and jump, was known to miss the break, and had a penchant for going extremely wide in his races. So intractable a pupil was he that Jones called him the “dumbest horse I ever trained.”

Despite his misadventures, he managed to win seven of 16 races as a juvenile, including the Hopeful S., Saratoga Special and Breeders’ Futurity. He ruined his chances in the Pimlico Futurity, however, after careening wide on both turns, and was beaten five lengths into third. His record was still good enough to earn him a share in the honors as co-champion two-year-old with Our Boots, who had defeated Whirlaway in three of their four meetings, including the Futurity S. at Belmont.

In the spring of Whirlaway’s three-year-old season in 1941, Calumet maestro Warren Wright was pushing for him to run in the prestigious Flamingo S., but Jones strongly felt that he needed a sprint instead. Jones was not about to follow the expected path if his colt required something different, and in the mark of an outstanding horseman, he made the program to suit the horse, not forcing the horse to fit a cookie-cutter program. So Whirlaway contested four allowance sprints in Florida, winning two, and captured an ordinary six-furlong handicap at Keeneland.

Whirlaway wins the 1941 Kentucky Derby
Whrilaway winning the Kentucky Derby (Courtesy of the Kentucky Derby/Churchill Downs)

The head case, though, had still not absorbed his lessons, and he continued to bear out, which contributed to his six-length loss to his nemesis Our Boots in the Blue Grass S. He pulled a similar self-defeating stunt in the Derby Trial, when he nullified his blistering move on the far turn by drifting to the far outside and wound up second by three-quarters of a length.

These accounts of Whirlaway’s behavior make Fusaichi Pegasus look like a model of deportment. But instead of dismissing him as a hopeless mess, Jones called upon his renowned patience and acute powers of observation to keep diagnosing Whirlaway’s ills and devising appropriate remedies. In short, Jones treated him as a continual work in progress, and the trainer wrote another curriculum tailor-made for his problem student.

Warren Wright summed up Jones’ approach best.

“One doesn’t employ a system in raising an unusual child,” Wright was quoted as saying in the Thoroughbred Record. “One studies the child, watches nervous reactions, follows awakening interests, or in other words, carefully bends the twig.”

Jones devoted lavish amounts of time to his colt, accompanying him, schooling him, working him, relaxing him. It’s a truism that great trainers are known for their attention to detail, and Jones’ painstaking efforts led him to make an inspired equipment change to Whirlaway’s blinkers for the Kentucky Derby, cutting away the cup on his left and leaving the right eye covered, reasoning that this would curtail his drifting. The other part of the solution was to get future Hall of Famer Eddie Arcaro in the irons.

In a daring experiment to familiarize Arcaro with Whirlaway in a workout, Jones, astride his pony, took up a position a few paces off the inside rail on the far turn, right where the colt would tend to go wide, and he told the jockey to steer Whirlaway between the rail and the pony. Just as Jones boldly surmised, the colt cornered beautifully.

The stage was set

The stage was set for an historic Kentucky Derby. Undeterred by his idiosyncrasies, the betting public sent Whirlaway off as the nearly 3-1 favorite. Away slowly and boxed in traffic, he dropped back as expected in the early going. Arcaro shrewdly threaded him between horses as he vaulted into contention on the far turn. With his customized headgear and his new partner at the helm, there was no question of frittering away his advantage this time. Whirlaway’s breathtaking acceleration swept him to the front, firmly putting Our Boots in his place. Echoing his sire, who kept increasing speed as he approached the line at Epsom, Whirlaway poured it on in the final furlong and crossed the wire eight lengths in front while breaking Twenty Grand’s track record. Whirlaway’s mark of 2:01 2/5 would stand for 21 years.

Whirlaway wins the 1941 Kentucky Derby
Whirlaway (Courtesy of the Kentucky Derby/Churchill Downs)

The Triple Crown lay at his mercy. Sauntering out of the gate again in the Preakness and galloping at least six lengths behind the next-to-last runner on the backstretch, Mr. Longtail turned on the afterburners and circled the entire field by the quarter pole, gearing down to win by 5 1/2 lengths in the end. He again drubbed Our Boots, proving the point that two-year-old form is often turned upside down at three.

The Belmont was a cakewalk. His three overmatched foes conspired to slow the pace, vainly attempting to take the starch out of his kick. Arcaro was too canny to fall for the tactic, reportedly saying, “The hell with this, fellas, I’m leaving.” Whirlaway seized the race by the throat before they’d gone halfway and strolled home by 2 1/2 lengths unextended.

The Longtail

A marvel of soundness and physical hardiness, Mr. Longtail raced a total of 20 times at three, winning 13 and placing in the remaining seven. He earned a staggering $272,386 during the 1941 season, reportedly more than any other entire stable of runners. In addition to the Triple Crown, he
captured such significant prizes as the Dwyer S., then contested at Aqueduct; the American Derby; the Travers S., toting 130 pounds, in classic, swashbuckling Whirlaway style, rocketing from 11 lengths back; and the 1 5/8-mile Lawrence Realization S., in which he actually set the pace en route to a ludicrously easy eight-length victory. His most valiant loss came in his seasonal finale, the two-mile Jockey Club Gold Cup. Mr. Longtail waged a no-holds-barred battle with Market Wise throughout the stretch and just missed by a nose, but Market Wise had to set a new American record of 3:20 4/5 to beat him.

Perhaps the most revealing image of Whirlaway’s three-year-old campaign is the photo-finish of his dramatic win in the Saranac H. at Saratoga, a picture worth the proverbial thousand words. Resorting to his old tricks, he drifted to the far outside, while the game speedster War Relic scraped the paint on the inside. Whirlaway overcame his wide trip as well as his 130-pound impost, 13 more than War Relic, to get up by a whisker in the last jump. The photo-finish image shows the vast gap between War Relic hugging the rail and Whirlaway streaking impossibly wide, a fine summation of both his travails and his ultimate triumphs.

In the wake of Pearl Harbor…

Whirlaway was acclaimed Horse of the Year, a title that he would successfully defend during his four-year-old season. Over the winter, he took up residence in California with an eye toward kicking off his 1942 campaign there, but America’s entry into World War II scuttled those plans.

In the wake of Pearl Harbor, the authorities were gravely worried about the possibility of other attacks on populated areas on the West Coast. Security concerns led to the cancellation of the winter meeting at Santa Anita, and at one stage, the track was used in the infamous internment of Japanese Americans. Whirlaway had to ship back East, but with military transportation needs obviously taking precedence, his travel arrangements were delayed.

“Whirlaway at four was still small in stature, long in tail and big in heart.”

The Blood-Horse

Despite the later than projected start to his season, Mr. Longtail ran 22 times, winning 12 and placing in the other 10, an especially remarkable scorecard considering that he was regularly giving away weight to his rivals. Many of his triumphs were accomplished in his patented come-from-the-clouds manner, including the Massachusetts H., in which he set a new track record of 1:48 1/5 for the 1 1/8 miles and surpassed Seabiscuit’s earnings total to become the world’s leading money winner. Although the
supremely talented three-year-old Alsab defeated him in two of their three meetings, most famously by a diminishing nose in their celebrated match race, Whirlaway still took Horse of the Year honors as the first equine to earn more than $500,000. As the Blood Horse described him, “Whirlaway at four was still small in stature, long in tail and big in heart.”

An effort was made to race him at five, but he was injured in his second start, visibly in pain on the gallop-out. The time had come to call it a career, with a final tally of 32 wins, 15 seconds and nine thirds from 60 starts, and $561,161 in earnings. He was out of the money only four times, thrice as a juvenile and in his injury-marred last outing.

Reporting for Duty

Originally retired to stud at Calumet Farm, Whirlaway was later recruited by the great French breeder Marcel Boussac. At Boussac’s farm in the French countryside, he died at the relatively young age of 15 in 1953. Mr. Longtail was enshrined into the Hall of Fame in 1959.

Whirlaway was not a scintillating sire, but he left a few good fillies to carry on his blood. Through his daughters, he appears in the pedigrees of three-time Horse of the Year Forego; 1978 champion older female Late Bloomer (Stage Door Johnny), who was also a good broodmare; 1987 Belmont S. (G1) winner Bet Twice; and current Grade 1 performer Alphabet Kisses (Alphabet Soup).

The daughter who’s done the most to ensure the survival of Whirlaway’s blood is Rock Drill, dam of 1966 champion three-year-old filly Lady Pitt (Sword Dancer). Lady Pitt is a significant ancestress of many contemporary stakes winners, including a bevy of Phipps homebreds ranging from the 1989 Breeders’ Cup Sprint (G1) hero, Dancing Spree, to the 1994 champion three-year-old filly, Heavenly Prize (Seeking the Gold). Another branch of descent from Lady Pitt culminates in one of this year’s talented three-year-olds, Sorcerer’s Stone (Gulch), who had Kentucky Derby (G1) aspirations before being sidelined by injury this week

Ever popular because of his startling come-from-behind style and his distinctive flying tail, Whirlaway will be remembered as a charismatic champion who maintained an impeccable standard of performance over time. Ben Jones will equally be remembered as the thoughtful and persevering horseman who invested countless hours to transform Whirlaway from a flawed prototype into a racing machine.