The Derby


These pampered racegoers were treated to a race whose unpredictability, drama, and display of superb horsemanship set the standard for the Derby. The favorite was Chesapeake, a come-from-behinder trained by the profoundly gifted Ansel Williamson, a former slave. To ensure that the front-runners would exhaust themselves early in the race, Williamson had honed the speed of Chesapeake’s stablemate, Aristides, then entered him in the Derby as a rabbit. The strategy worked, but not as Williamson anticipated. Aristides set a blistering pace, fought off his challengers, then was eased up to wait for his stablemate. But Chesapeake, compromised by a poor start, never came. Remarkably, Aristides had something left. Urged on again, he repelled the closers and won. His time was an American record, and the Derby was off to a rousing start.

For the next several years the Derby was a success, attracting huge crowds and the nation’s best horses. Clark absorbed himself in designing dazzling fetes for his wealthy patrons, and his track became the place to be for high society. The moneyed set warmed to the attention, but at a cost. Clark reportedly focused entirely on his well-heeled patrons, leaving details of track operations to incompetent subordinates. Churchill Downs never turned a profit.

Then, in 1886, a petty squabble nearly ended the Derby. It began when bookmakers who refused to pay the track their operating fees were locked out on Derby Day. James Ben Ali Haggin, a high-rolling New York gambler and influential owner, had brought a huge string of horses to Churchill Downs for the season. Though he was upset at the absence of bookmaking, he ran his namesake, Ben Ali, in the Derby and watched him win it. He then announced that if bookies didn’t return, he would pack up his horses and leave. The threat carried considerable weight; without Haggin’s fine horses the 1886 Churchill Downs season, as well as the 1887 Derby, would be seriously diminished. Within hours crisis seemed to be averted when the bookies reached a settlement with the track. But the triumph was undercut by a track official, who told listeners in no uncertain terms where Haggin could go. Word of the statement reached Haggin that night. By dawn his barn was empty.


Haggin meant business. Back in New York he persuaded all the Eastern horsemen, whose runners dominated racing, to join a boycott of Churchill Downs. The impact was staggering. Kentucky’s horses were not yet the cream of the industry they would later become, and they couldn’t carry the track or the Derby. Interest in the race plummeted, and its fields shrank to three or four woeful entries. Clark struggled on without pay, covering thousands of dollars in debts out of his own pocket. But Churchill Downs drifted deep into the red, and by early 1894 the Louisville Commercial was referring to the Derby as “a contest of dogs.” That August the track went bankrupt, and Clark, utterly despondent, left its helm. He never recovered. Five years later he was found dead in a hotel room, the pistol still in his hand.

A group of investors obtained Churchill Downs and renovated it with a new grandstand featuring the now-signature twin spires. The race distance was cut to a mile and a quarter—a particularly formidable distance requiring both speed and stamina—and the track began draping the winner in roses, a tradition that later inspired the race’s nickname, Run for the Roses. But the boycott continued. Worse, management slashed purses. Trainers took their better animals away in search of bigger purses, attendance sank further, and Derby fields remained tiny and poor. In 1902 the managers gave up and looked for someone on whom to dump their white elephant.

The man they found was an unlikely deliverer, a merchant tailor named Col. Matt J. Winn. At the age of thirteen, upon witnessing Aristides’ Derby triumph from his father’s grocery wagon, Winn had been smitten with the race and had seen every running since. He had no experience managing a track, but he was endowed with irresistible charm and uncanny business sense. Taking over as vice president and later as general manager, Winn began by making personal appeals to Louisvillians who had once frequented the track, offering them choice seats at the 1903 Derby. The campaign worked. Erstwhile fans brought loads of friends to the race, and Winn entertained them so well that they kept coming back. For the first time Churchill Downs made a profit. It continued to run in the black in succeeding years, and though the Derby couldn’t seem to draw more than six modest, locally based horses, things looked promising.