Groom Ernest Shackleford described Sysonby as "a common, cheap-looking, lop-eared colt that stood only 15.1 hands as a three-year-old." Yet his legendary name, derived from that of a hunting lodge, dominates early twentieth century racing history. Horsemen who witnessed his career spoke of Sysonby in tones of awe. Some named the champion as the best they ever saw, ranking him above even Man o' War.

Sysonby's dam, Optime, was by Orme, a son of English Triple Crown winner Ormonde. Her owner, Marcus Daly, bred her to Epsom Derby winner Melton. He didn't live to see her foal, however. Following his death, his horses were shipped from England to New York and sold at auction, where James R. Keene paid $6,600 for the mare, and became breeder of record for her colt foaled in 1902.

James R. Keene raced his horses both in England, where he had won the 1882 Ascot Gold Cup with Foxhall, and the United States, where his stars had included 1901 Horse of the Year and Belmont Stakes winner Commando, 1904 Belmont Stakes winner and champion Delhi, and the great Domino, whom he raced in partnership with his son. Evaluating his yearlings in 1903, Keene decided to sell one small, unattractive, and seemingly slow bay colt. His son convinced him to keep the horse, and named him Sysonby.

A year later, Sysonby was scheduled to be sent to England. Trainer James G. Rowe, Sr. didn't want to lose the little bay, and brought him out wrapped in blankets and bandages, telling Keene that he feared for the colt, who was too sick for the voyage. The owner relented, and Sysonby stayed to race for Rowe with Keene's American stable. Had he gone to England he almost surely would have survived, and probably would have scored a classic victory or three.

While the trainer's story of illness had been false, his private evaluation of the colt was correct, for he won at first asking, taking a five and a half furlong event at Brighton Beach by six lengths.

Only two days later, Sysonby won the Brighton Junior Stakes by four lengths. When he arrived in Saratoga, the flying bay colt reeled off six length victories in both the Flash Stakes and the Saratoga Special.

Sysonby had won four straight races, all by at least four lengths, when he was entered in the Futurity at Sheepshead Bay. Bettors made him the favorite at 3 to 2, despite the high weight of 127 pounds and challengers such as future classic winners Agile and Tanya, the great filly Artful, Canadian champion Oiseau, and the unbeaten Tradition. It was said to be the toughest field the famous race had ever seen.

When Artful pulled off a five length win, the crowd was shocked. Sysonby had never challenged her, and was nosed out of second place by Tradition. One of Keene's grooms later admitted to drugging the young star for personal profit. That fact made the show finish seem a heroic deed; few horses could run that well full of tranquilizers.

A three length victory in the Junior Champion Stakes, in which he covered six furlongs in 1:09 3/5, ended the season for Sysonby, and he was named Champion Two Year Old Colt. Artful's victory in the Futurity, together with her undefeated status, was rewarded with the title of Champion Two Year Old Filly.

In his first start as a three-year-old, Sysonby was asked to give weight to older horses in the Metropolitan Handicap. Carrying 107 pounds, he dead heated with Race King, a five-year-old carrying only 97 pounds, in a time of 1:41 3/5. The third place horse was another five lengths back.

Next he returned to Sheepshead Bay, the scene of his only defeat the previous season. He won the mile and a quarter Tidal Stakes by five lengths in 2:05, beating Kentucky Derby winner Agile, then won the Commonwealth Handicap at the same distance by four lengths.

Sysonby met the Belmont Stakes winning filly Tanya in the Lawrence Realization and beat her by five lengths. He covered the mile and five eighths in 2:47 with hardly an effort, and was eased in the stretch.

Sysonby returned to Brighton Beach, where his career had begun, and cantered to victory in the Iroquois Stakes. In the Brighton Derby nine days later, he beat Agile by five lengths, again without much effort, while the Kentucky Derby winner in turn beat third place finisher Pasadena by thirty lengths.

In Saratoga's Great Republic Stakes, worth $50,000, Sysonby recovered from a bad start to win by three lengths over Oiseau and Broomstick. Seven days after winning the Century Stakes, again beating Broomstick as well as the champion mare Eurgenia Burch, Sysonby came home the four length winner in the two and a quarter mile Annual Champion Stakes at Sheepshead Bay. Oiseau and Broomstick gave chase, to no avail.

Sysonby had swept through a nine race season undefeated, winning at distances from a mile to two and a quarter miles. His superiority was unchallenged, and he won every start easily. Except for the dead heat, he had never even been headed. Sysonby was named Horse of the Year, as well as champion three-year-old colt, and had earned $184,438 in his fifteen race career.

In June of 1906, Sysonby became the victim of variola, or possibly a liver disease, dying in his stall at Sheepshead Bay. Over four thousand people turned out to attend his burial in front of Keene's stables and to pay tribute to the great horse. Sysonby was later exhumed, and his skeleton has been on display since 1907 at the American Museum of Natural History in New York City. Sysonby became a member of the Hall of Fame in 1956.

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