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In the days long before the Breeders’ Cup and other major racing events that offered excellent purses to fillies and mares, they frequently competed against colts, even in the most prestigious races. And they sometimes won.

One such result came in the 1904 Futurity Stakes, then run at Sheepshead Bay racetrack. Henry Duryea had leased the daughter of Hamburg from the estate of breeder WC Whitney, but the filly came into the Futurity without much fanfare or much knowledge of her ability outside of her stable.

Yet Duryea’s trainer John Rogers expected her to win the race, even though it was chock full of high-class racers, including the unbeaten Sysonby, as well as top talent like Tradition and Tanya.

In the race report for the Futurity, the New York Tribune reported that “For weeks the shrewd watchers of morning gallops have whispered to those who paid to listen that the Duryea outfit had a ‘trick’ in its string other than the beautiful Tanya, with which it had won the National Stallion, the Hopeful, and the Spinaway.”

The Tribune also reported that the stable had intentionally won with a stablemate of Artful’s at Saratoga to keep the filly’s maiden weight allowance for consideration in the Futurity, where she carried 114 against 127 on Sysonby and Tradition, 124 on Tanya.

But to the general public, as well as to the racing professionals, the horse of horses in the Futurity was James R Keene’s Sysonby, an English-bred son of Melton that Keene ranked as highly as his beloved Domino. The Tribune noted: “They had seen that amazing lop-eared giant from across the seas slip through the backstretch of Brighton his first time out with the speed of a ghost; they had seen him run a quarter at Saratoga in :22 1/5 seconds on his own courage — losing Hot Shot and Britisher as an antelope would lose a beagle on the bounding prairies, and they could not get away from him nor close their eyes to those fleeting glimpses they had had of him.”

As a result, Sysonby was the odds-on favorite, and the Duryea trio of Artful, Tanya, and Rose of Dawn was 5-2 second choice. The Tribune reporter described the idolatry of Sysonby’s admirers thus: “In the paddock Sysonby, big, lusty and indifferent, his ears drooping in indolent disregard of the adulation of his worshippers, was surrounded by an awe-stricken circle of men and women.”

When the 16 juveniles rocketed down the Futurity course for six furlongs in a fierce battle of speed between the top colt and filly, Artful stopped the clock in 1:11 4/5, the fastest for the race over that course. The filly won by four lengths from Tradition, who had come on through the stretch to catch a tired Sysonby by a half-length. Tanya was fourth. [The next year she won the Belmont Stakes.]

There were possible explanations for Sysonby’s loss, including a groom’s confession to drugging the colt before the Futurity, and these came to seem of greater consequence when the colt proceeded to win all his remaining races. Artful did the same, retiring with six victories from eight starts. Sysonby was victor in 14 of 15. Both were inducted into the National Museum of Racing and Hall of Fame in 1956.

But on that August evening in 1904, the only thing that mattered to the Duryea stable was that Artful had rolled home the winner.