The Heart That Wears the Crown: Whirlaway

June 2nd, 2023

The 13 horses that have worn the crown over the past century all come to their thrones via different paths. From starting as a Derby Day maiden to sealing their crown after only a handful of starts, each stands as a shining example of what the Thoroughbred is capable of: the speed, stamina, and heart necessary to turn back all challenges on the sport’s biggest stages. To win this elusive title is not done in just one style. Rather, each brings his own certain something to the list.

Whirlaway, the fifth Triple Crown winner, ignited the imaginations of those along for the ride on the cusp of war in 1941. With his distinctive long golden tail and single-cup blinker, “Mr. Longtail” was a picture of both quirkiness and durability, trying the patience of his trainer and capturing the hearts of racing fans everywhere with his blazing final run to the wire.

Eyes on the Prize

Warren Wright wanted more than anything for the devil red and blue silks of Calumet Farm to grace the winner’s circle in America’s classic races, especially the Kentucky Derby. The Wrights had already journeyed to Churchill Downs with Nellie Flag, fourth behind Omaha in 1935, and Bull Lea, eighth behind Lawrin in 1938. Wright’s investment in Blenheim II gave him the chance to breed classic winners of his own, so he paired Dustwhirl, an unraced daughter of Belmont Stakes winner Sweep, with the newly imported stallion in the hopes that this foal might finally be the one.

When Dustwhirl’s foal came into the world, the chestnut colt that would become Whirlaway proved to be easygoing but mischievous, throwing his head around during grooming. He also zoomed around the Calumet paddock with other mares and foals, often beating the others with ease. The humans around him noticed that he was growing into a fine-looking Thoroughbred, with ample bone and muscle that hinted at his potential. As he approached his second birthday, Dustwhirl’s colt left behind the pastoral scenes at Calumet and started his career as a racehorse.

The transition from the familiar greens of farm life to the bustle of the racetrack was not an easy one for Whirlaway. He proved to be stubborn, insisting on leaving the backside and returning to the barn through the same gate, and rebelling if he did not. He resisted saddling and would often require multiple sets of hands to prepare him for a workout. Yet the colt showed bottomless potential and an unlimited supply of energy, thriving on racing and training. Trainer Ben Jones took Dustwhirl’s colt in hand and schooled Whirlaway himself. They walked the racetrack, stood by as other horses worked, spent time in the starting gate, and practiced saddling and unsaddling.

The question was, would all of Jones’ hard work pay off? Could he rein in that willfulness just enough to get the colt to focus on his job and use that prodigious speed and stamina on race day? Only time would tell.

Singular Talent

Early in his career, Whirlaway was noted for how much he would bear out during a race, especially around turns. Jones attributed this tendency to go toward the outer rail during a race to two things: In his earliest races, the colt saw the gate that led to the backside and ran toward that, saved only by the intervention of his jockey to stay on task, and second, the speed that the son of Blenheim II took the turns tended to force him outward. But Jones had a solution for both.

Prior to the Kentucky Derby, the trainer had found the right rider for Calumet’s new hope for roses, Eddie Arcaro, but not a solution for the bearing out just yet. He decided to try outfitting Whirlaway with blinkers, a common tactic for horses that need to focus during a race, but made one alteration: he cut off the cup for the inside eye and left the outside one on. The colt could see the inside rail but not the outside one, with the aim of keeping him focused on running straight. Jones and Arcaro tested this one morning during Derby week. The trainer and his pony sat several feet out from the rail, a gap that he told Arcaro to take the colt through. Wearing the one-eyed blinker, Whirlaway followed orders, the jockey easily guiding him through the space between the trainer and the rail.

With that in place, Arcaro and Whirlaway faced a field of 10 others with his new blinkers and another secret weapon: that blazing final kick that became his trademark. As they entered the stretch, the Calumet colt was fourth, Arcaro moving him to the rail and giving Whirlaway the cue. With his ears pinned back, he moved so fast that the other horses seemed to be standing still in those last furlongs, pulling away to win by eight lengths.

The next two Triple Crown classics would be his in similar style, with the Calumet champion throwing in a win against older horses in between the Preakness and Belmont. Those wins started fans’ love affair with the chestnut colt, one that would endure long past that day at Churchill Downs.

Long-Tailed Legacy

Trainer Ben Jones left Whirlaway’s distinctive golden tail long to discourage horses from running on his heels, and while it might have been intended as an athletic advantage, the sight of his tail billowing out behind coming down the stretch was one that fans across the country fell in love with. Crowds turned out wherever he raced, cheering him on every time he entered the starting gate. From California to Chicago to Calumet, Whirlaway was a superstar in his time, and Warren Wright and others used that stardom to help raise money for the war effort as America entered World War II in December 1941. In all, his 22 races toward that end raised $5 million, the patriotism of racing fans and their love for the long-tailed colt at the heart of their generosity.

The four before him all made the Triple Crown their own, from Sir Barton’s surprising trip through the three races to War Admiral’s courage in finishing the Belmont after injuring himself at the start. Whirlaway followed in their footsteps, presaging Secretariat’s whirlwind trip from Louisville to Baltimore to New York. “Mr. Longtail” showed his challengers both his blazing speed and beautiful tail, and earned his crown with ease, leaving great memories of his exploits in his wake as he brought Calumet Farm to the heights that remain legendary in the sport of horse racing.