The Derby

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In 1941 came Whirlaway. The chestnut horse with the exceptionally long tail was the most eccentric personality to make his mark on the Derby. He was, said his trainer Ben Jones, as “nervous as a cat in a room full of rocking chairs.” He was known to make sudden ninety-degree turns toward the crowd in mid-race, zigzag drunkenly, and run whole races along the outside rail, losing massive amounts of ground as he blew past the grandstand inches from amazed fans. (He often won anyway.) Even his jockey, Eddie Arcaro, admitted that he was terrified of the colt. Yet even as he invariably took the scenic route around the track, Whirlaway could unleash a closing rally that was absolutely scorching. Arcaro described him as a “blinding tornado. . . . What a horse! What a horse!”

IN 1925 THE DERBY’S first radio broadcast drew five or six million listeners, estimated to be the largest radio audience ever; in 1931 half the nation tuned in.

But Jones knew Whirlaway would lose the Derby if he kept careening all over the course. He tried everything to reform him; during one workout, Jones ordered an intimidated Arcaro to charge Whirlaway through a razor-thin gap between a standing pony and the rail. Before the Derby, Jones walked Whirlaway along the inside rail, then took him to the outer rail in hopes of satisfying his insatiable curiosity about spectators. Then, minutes before the race, Jones cut away the left eye cup on the colt’s blinkers, hoping that opening the horse’s vision to the inside would help him resist the urge to buzz the crowd.

Leaving the gate, Whirlaway and Arcaro dropped behind the field. On the far turn a hole leading into the pack opened before them. Arcaro had a weighty decision to make: dive into the hole and risk being blocked while moving at terrific speed, or lose ground circling the pack and face the possibility that Whirlaway would pay the crowd a visit. Arcaro chose the former and charged Whirlaway into the gap. In a moment of supreme drama, Whirlaway darted into the back of the pack and disappeared from view. A second later he came roaring out the other side, pouncing forward with such force that Arcaro nearly tumbled backward out of the saddle. ”... I felt as if I were flying through the air,” the jockey told Peter Chew, author of the splendid The Kentucky Derby: The First 100 Years . Whirlaway hit the lead and kept rolling, arrow straight, to an eight-length victory. His record time of 2:012/5 would stand for twenty-one years. Whirlaway went on to win the Triple Crown.

In his eighties but vigorous as ever, Matt Winn guided the Derby through the 1940s. From an infield tower he watched a remarkable procession of gifted horses, including eventual Triple Crown winners Count Fleet and Assault, sail to Derby victories. In 1948, with the emphatic victory of soon-to-be Triple Crown champ Citation, he hosted his greatest runner yet. Winn’s job was done. In 1949 the man who compared his seventy-five Derbies with rosary beads, “always before me, always vivid, with every detail silhouetted in the light of the vanished years,” died.

With Winn’s death the Derby reached an odd turning point. Year after year great horses had paraded through Louisville and, after clean racing trips, emerged as champions. A single generation had seen eight horses sweep the Triple Crown; one arrived every few years with clockwork regularity. But in the 1950s the unexpected became the rule. It began in 1953, when the wildly popular, wonderfully telegenic Native Dancer, the Derby’s first television star, was bumped, checked, and blocked into a heartbreaking head loss, the only race in which he was ever beaten. The unthinkable recurred in 1955, when the seemingly unbeatable Nashua was hoodwinked by Swaps, a California speedball whose owner slept in a stall to be near him. Two years later the unexpected gave way to the truly bizarre. A few days before the Derby, the owner of the great Gallant Man dreamed that he saw his colt leading the Derby down the stretch. The dream then became a nightmare. Just before the wire Gallant Man’s jockey inexplicably pulled up, slowing the horse and costing him the race. Sure enough, on Derby Day, Gallant Man rocketed down the Derby stretch and seized the lead, looking like a winner until the jockey, Bill Shoemaker, misjudged the sixteenth pole as the finish, pulled up and stopped urging his mount momentarily, and lost by a nose. The Derby’s era of the oeculiar was far from over.